Triethylamine → Boc-Tyr(OBn)-Ser(OBn)-CO2Me

HRID 355521

反応式

HRID 355521 の反応式
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18](O)=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.C1C=C2N=NN(O)C2=CC=1.O.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:54][C@H:55]([C:65]([C:67]([O:69][CH3:70])=[O:68])=[O:66])[CH2:56][O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1.FC(C(O)=O)(F)F.CCN(CC)CC>CCOC(C)=O>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([NH:54][C@H:55]([C:65]([C:67]([O:69][CH3:70])=[O:68])=[O:66])[CH2:56][O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 27960291-Hydroxybenzotriazole hydrateHCID 131720920Ser(OBn)-CO2Me.TFA

生成物 1

HCID 131720919Boc-Tyr(OBn)-Ser(OBn)-CO2Me収率 73%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of Boc-Tyr(OBn) (1.88 g, 6.50 mmol) in EtOAc (30 mL) at 0° C. was added HOBT hydrate (1.19 g, 7.80 mmol) followed by DCC (1.61 g, 7.80 mmol). A solution of Ser(OBn)-CO2Me.TFA (2.1 g, 6.50 mmol) in EtOAc (20 mL) was added followed by Et3N (1.09 mL, 7.80 mmol). The mixture was allowed to warm to room temperature and stirred overnight. The mixture was filtered, diluted with EtOAc, and washed twice with saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated. Flash chromatography (40% EtOAc/hexane) gave 2.67 g (73%) of the title compound as a white solid, mp 81°-84° C.

後処理

  1. filtrationThe mixture was filtered
  2. additiondiluted with EtOAc
  3. washwashed twice with saturated aqueous NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-b912eaba23384d21b5d4e1751cf41837
出典データセット
uspto-grants-1998_11
特許番号
US05830868

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