Benzyl chloroformate → (S,S)-2,7-Bis(tert-butyloxycarbonylamino)-4-benzyloxycarbonyl-4-azaoctanedioic acid

HRID 976024노트

반응식

HRID 976024 반응식
C([O-])(O)=O.[Na+].[CH2:6]([O:13][C:14](Cl)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:17]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][NH:30][CH2:31][CH2:32][C@H:33]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:34]([OH:36])=[O:35])[C:26]([OH:28])=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18]>O1CCOCC1.O>[C:17]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][N:30]([C:14]([O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:15])[CH2:31][CH2:32][C@H:33]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:34]([OH:36])=[O:35])[C:26]([OH:28])=[O:27])=[O:23])([CH3:19])([CH3:20])[CH3:18]

참가 물질

6

반응물 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 57285280(S,S)-2,7-Bis(tert-butyloxycarbonylamino)-4-azaoctanedioic acid

생성물 1

HCID 57047504(S,S)-2,7-Bis(tert-butyloxycarbonylamino)-4-benzyloxycarbonyl-4-azaoctanedioic acid

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
0 °C

실험 절차

1M NaHCO3 (5.9 ml, 5.92 mmol ) and benzyloxycarbonyl chloride (0.5 g, 0.42 ml, 2.96 mmol) were added to a solution of (S,S)-2,7-bis (tert-butyloxycarbonylamino)-4-azaoctanedioic acid (0.6 g, 1.48 mmol) in dioxane (40 ml ) and H2O (30 ml ) at 0° C. The mixture was stirred at 0° C. for 3 hours, at ambient temperature for 6 hours, evaporated, the residue triturated with chloroform (5 ml) and acetic acid to pH 5. The chloroform solution was evaporated and the product isolated after chromatography on silica gel (CHCl3 : MeOH 4:1).

후처리

  1. customevaporated
  2. customthe residue triturated with chloroform (5 ml) and acetic acid to pH 5
  3. customThe chloroform solution was evaporated
  4. customthe product isolated after chromatography on silica gel (CHCl3 : MeOH 4:1)

출처 및 근거

ORD 기록
ord-3c82f7f9457e42389d94d1091b384c90
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05610141

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