Hydrochloric Acid → Boc-Thr(Bzl)-Ser(Bzl)-Ser(Bzl)-Glu(OBzl)-OH

HRID 26331ノート

反応式

HRID 26331 の反応式
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:12]([NH:14][C@H:15]([C:25]([NH:27][C@H:28]([C:41]([OH:43])=[O:42])[CH2:29][CH2:30][C:31](=[O:40])[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:26])[CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[NH:52]([C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[C@H:53]([C:64]([O:66]N1C(=O)CCC1=O)=O)[C@@H:54]([CH3:63])[O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1.CCN(CC)CC>C1COCC1.CN(C=O)C.CS(C)=O>[NH:52]([C:74]([O:76][C:77]([CH3:78])([CH3:79])[CH3:80])=[O:75])[C@H:53]([C:64]([NH:1][C@H:2]([C:12]([NH:14][C@H:15]([C:25]([NH:27][C@H:28]([C:41]([OH:43])=[O:42])[CH2:29][CH2:30][C:31](=[O:40])[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:26])[CH2:16][O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:66])[C@@H:54]([CH3:63])[O:55][CH2:56][C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2 回HCID 12879029Boc-Thr(Bzl)-OSuHCID 131711277Boc-Ser(Bzl)-Ser(Bzl)-Glu(OBzl)-OH

生成物 1

HCID 131711276Boc-Thr(Bzl)-Ser(Bzl)-Ser(Bzl)-Glu(OBzl)-OH

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Boc-Ser(Bzl)-Ser(Bzl)-Glu(OBzl)-OH (71.6 g, 104 mmol) was treated with 2.7 liters of freshly prepared 3.9 N HCl in THF for 45 minutes. The mixture was evaporated to dryness and the residue evaporated twice more with THF to give a solid mass (59.3 g; mp 161°-165°). It was collected and washed with ether and stirred in 500 ml of DMF with Boc-Thr(Bzl)-OSu (38.2 g, 94 mmol) in the presence of Et3N (25 ml) at 0° for 1 hour and then at 25° for 15 hours. More Et3N (14.5 ml) was added in serveral portions during this time to maintain the reaction slightly basic. Some insoluble matter formed was filtered off and the filtrate evaporated to an oil which was dissolved in EtOAc (1.5 liters), washed with 5% HOAc, H2O (2 times), dried (Na2SO4), and evaporated to a solid mass. The product was recrystallized from EtOAc and petroleum ether to yield, 64.8 g (78.1%); mp 115°-118°; [α]D25 =+11.64° (c 1, DMSO).

後処理

  1. customThe mixture was evaporated to dryness
  2. customthe residue evaporated twice more with THF
  3. customto give a solid mass (59.3 g; mp 161°-165°)
  4. customIt was collected
  5. washwashed with ether
  6. temperatureto maintain
  7. customthe reaction slightly basic
  8. customSome insoluble matter formed
  9. filtrationwas filtered off
  10. customthe filtrate evaporated to an oil which
  11. dissolutionwas dissolved in EtOAc (1.5 liters)
  12. washwashed with 5% HOAc, H2O (2 times)
  13. dry with materialdried (Na2SO4)
  14. customevaporated to a solid mass
  15. customThe product was recrystallized from EtOAc and petroleum ether
  16. customto yield

出典と根拠

ORDレコード
ord-5b86cc1232fb4c7090a131188ab81147
出典データセット
uspto-grants-1979_04
特許番号
US04148788

反応ノート

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