Acetic Anhydride → HCID 69101484, compound

HRID 394027Notes

Reaction equation

HRID 394027 reaction equation
[NH2:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:28])[CH2:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:4]([C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C@@H:32]2[C:36]([NH:38][CH2:39][C@H:40]2[CH2:45][CH2:44][CH2:43][N:42]([CH2:46][CH:47]3[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]3)[CH2:41]2)=[O:37])=[O:30])[CH2:3]1.[C:53](OC(=O)C)(=[O:55])[CH3:54]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:53]([NH:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:28])[CH2:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:4]([C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C@@H:32]2[C:36]([NH:38][CH2:39][C@H:40]2[CH2:45][CH2:44][CH2:43][N:42]([CH2:46][CH:47]3[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]3)[CH2:41]2)=[O:37])=[O:30])[CH2:3]1)(=[O:55])[CH3:54]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 12149962HCID 12149962, compound

Product 1

HCID 69101484HCID 69101484, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of 22 mg of (2R)-1-{(2S,4S)-4-amino-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonyl-N-{((3R)-1-cyclohexylmethyl-3-piperidyl)methyl}pyrrolidine-2-carboxamide in 1 ml of chloroform, 0.0089 ml of acetic anhydride and 0.0127 ml of pyridine were added at room temperature, followed by an hour's stirring at the same temperature. The reaction liquid was diluted with chloroform, washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. After distilling the solvent off under reduced pressure, the resulting residue was purified with a preparative thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), chloroform/methanol=8/1), to provide 18 mg of the title compound as a white solid.

Workup

  1. waitfollowed by an hour
  2. customThe reaction liquid
  3. washwashed successively with saturated aqueous sodium bicarbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter distilling the solvent off under reduced pressure
  6. customthe resulting residue was purified with a preparative thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), chloroform/methanol=8/1)

Sources & evidence

ORD record
ord-bb86723ab3164d44b285e353de7775b4
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

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