Sodium Carbonate → Fmoc-Thr(tBu)-Ser(tBu)-OBzl

HRID 523354

反応式

HRID 523354 の反応式
COC1CCCC1.[NH2:8][C@H:9]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:10][O:11][C:12]([CH3:15])([CH3:14])[CH3:13].C1C=CC2N(O)N=NC=2C=1.[NH:36]([C:48]([O:50][CH2:51][CH:52]1[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[C:58]2[C:53]1=[CH:54][CH:55]=[CH:56][CH:57]=2)=[O:49])[C@H:37]([C:45](O)=[O:46])[C@@H:38]([CH3:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41].CCN=C=NCCCN(C)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].[Na+].O.CN(C=O)C>[NH:36]([C:48]([O:50][CH2:51][CH:52]1[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[C:58]2[C:53]1=[CH:54][CH:55]=[CH:56][CH:57]=2)=[O:49])[C@H:37]([C:45]([NH:8][C@H:9]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:10][O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:46])[C@@H:38]([CH3:44])[O:39][C:40]([CH3:42])([CH3:43])[CH3:41]

参加物

9

反応物 6

HCID 10340Sodium CarbonateHCID 757711-HydroxybenzotriazoleHCID 138539Cyclopentyl methyl etherHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6364643N-(9-Fluorenylmethoxycarbonyl)-O-tert-butylthreonineHCID 53722581H-Ser(tBu)-OBzl

生成物 1

HCID 131735566Fmoc-Thr(tBu)-Ser(tBu)-OBzl

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To the CPME solution (35 mL) of H-Ser(tBu)-OBzl (2-OBzl(3,4,5-OPhy)-4-OMe) was added HOBt (71 mg, 0.43 mmol), Fmoc-Thr(tBu)-OH (1.00 g, 2.51 mmol), EDC.HCl (529 mg, 2.76 mmol) and DMF (10 ml) were added under ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, to the reaction solution was added 20% brine (30 ml) to give an organic layer and an aqueous layer. While stirring the obtained organic layer and aqueous layer, 10% aqueous sodium carbonate solution was added dropwise until the pH of the aqueous layer became 6.0, and the organic layer and the aqueous layer were partitioned (hereinafter this operation is sometimes to be abbreviated as “pH=6.0 washing”). The pH-6.0 washing was further repeated twice. The solvent in the obtained organic layer was evaporated under reduced pressure, the residue was dissolved in cyclohexane (40 ml), and the mixture was washed four times with 80% by volume of aqueous acetonitrile solution (30 ml) with stirring, and the organic layer and the aqueous layer were partitioned. The obtained organic layer was dried over sodium sulfate and filtered. The solvent in the obtained filtrate was evaporated under reduced pressure to give Fmoc-Thr(tBu)-Ser(tBu)-OBzl (2-OBzl(3,4,5-OPhy)-4-OMe).

後処理

  1. additionwere added under ice-
  2. temperaturecooling
  3. customAfter completion of the reaction
  4. customto give an organic layer
  5. additionwas added dropwise until the pH of the aqueous layer
  6. customthe organic layer and the aqueous layer were partitioned (hereinafter this operation
  7. washwashing”)
  8. washThe pH-6.0 washing
  9. customThe solvent in the obtained organic layer was evaporated under reduced pressure
  10. dissolutionthe residue was dissolved in cyclohexane (40 ml)
  11. washthe mixture was washed four times with 80% by volume of aqueous acetonitrile solution (30 ml)
  12. stirringwith stirring
  13. customthe organic layer and the aqueous layer were partitioned
  14. dry with materialThe obtained organic layer was dried over sodium sulfate
  15. filtrationfiltered
  16. customThe solvent in the obtained filtrate was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-47ff74d2bf5b49b4b9f30fe9177fb66e
出典データセット
uspto-grants-2016_05
特許番号
US09334302B2

関連ノート

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