Acetic Anhydride → HCID 67684739, compound

HRID 1901086Notes

Reaction equation

HRID 1901086 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:31]([N:33]1[CH2:38][CH2:37][C:36]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([OH:39])[CH2:35][CH2:34]1)=[O:32])[CH2:10][S:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:47](OC(=O)C)(=[O:49])[CH3:48]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:31]([OH:49])=[O:32])[CH2:10][S:11][C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2].[C:47]([O:39][C:36]1([CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:35][CH2:34][NH:33][CH2:38][CH2:37]1)(=[O:49])[CH3:48]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 57190214HCID 57190214, compound

Product 1

HCID 67684739HCID 67684739, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-t-butoxycarbonyl-S-trityl-L-Cysteinyl4-benzyl-4-piperidinol (100 mg, 0.16 mmol) in dry pyridine (2 ml), was added 4-dimethylaminopyridine (25 mg, 0.20 mmol) and acetic anhydride (0.030 ml, 0.32 mmol). The solution was heated to 50° C. (oil bath temp.) for 2 days and then allowed to cool to room temp. The reaction mixture was concentrated in vacuo and the residue partitioned between EtOAc and brine. The EtOAc layer was dried (MgSO4) and concentrated in vacuo to a brown oil. This material was purified by column chromatography on silica with 18-20% EtOAc/hexane as eluent. The appropriate fractions were combined and concentrated in vacuo to afford the product as a glassy solid.

Workup

  1. temperatureto cool to room temp
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue partitioned between EtOAc and brine
  4. dry with materialThe EtOAc layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo to a brown oil
  6. customThis material was purified by column chromatography on silica with 18-20% EtOAc/hexane as eluent
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13ff468cd579484db30e51ba650c09c9
Source dataset
uspto-grants-1996_11
Patent number
US05576313

Reaction notes

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