Acetic Anhydride → HCID 53782550, compound

HRID 1737016Notes

Reaction equation

HRID 1737016 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH2:8]([C@@H:15]1[CH2:20][C@@H:19]([N:21]([CH2:28][C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=[CH:31][CH:30]=2)[C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[CH2:18][CH2:17][N:16]1[C:39](=[O:49])[C@H:40]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[NH2:41])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[CH2:8]([C@@H:15]1[CH2:20][C@@H:19]([N:21]([CH2:28][C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=[CH:31][CH:30]=2)[C:22](=[O:27])[C:23]([F:26])([F:24])[F:25])[CH2:18][CH2:17][N:16]1[C:39](=[O:49])[C@H:40]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[NH:41][C:5](=[O:7])[CH3:6])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54152929HCID 54152929, compound

Product 1

HCID 53782550HCID 53782550, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

35 μl (0.376 mmol) of acetic anhydride are added to a solution of 180 mg (0.313 mmol) of the mixture of (2R*,4S*)-2-benzyl-1-((S)-phenylalanyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine diastereomers in 2 ml pyridine at 0°, and the mixture is stirred at 0° for 2.5 hours. The oily residue after evaporation in a rotary evaporator is taken up in methylene chloride, washed with 5% aqueous citric acid and with 1N sodium bicarbonate solution. The organic phases are dried over magnesium sulfate and evaporated to dryness. The title compound is obtained as white foam. TLC: methylene chloride/methanol/conc. ammonia (1000:50:1) Rf =0.39, FD-MS: M+ =616.

Workup

  1. customThe oily residue after evaporation
  2. customin a rotary evaporator
  3. washwashed with 5% aqueous citric acid and with 1N sodium bicarbonate solution
  4. dry with materialThe organic phases are dried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-c01f000e1b5440d79fb9de0ea636b130
Source dataset
uspto-grants-1996_07
Patent number
US05541195

Reaction notes

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