Acetic Anhydride → HCID 86640369, compound

HRID 1806886Notes

Reaction equation

HRID 1806886 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C@H:17]2[C@H:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=3[F:29])[C@:20]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=3[F:39])([C:30]#[N:31])[C@H:19]([CH2:40][C:41]([CH3:44])([CH3:43])[CH3:42])[NH:18]2)=[O:16])[CH2:10][CH2:9]1.C(OC(=O)C)(=O)C.C(N(CC)CC)C>C(Cl)Cl>[CH3:13][N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]([CH:17]2[CH:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=3[F:29])[C:20]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=3[F:39])([C:30]#[N:31])[CH:19]([CH2:40][C:41]([CH3:42])([CH3:44])[CH3:43])[NH:18]2)=[O:16])[CH2:12][C:2]1=[C:3]=[O:5]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86640368HCID 86640368, compound

Product 1

HCID 86640369HCID 86640369, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid piperidin-4-ylamide trifluoroacetic acid (80 mg, 0.10 mmol) in methylene chloride (10 mL), acetic anhydride (18 uL, 0.18 mmol) and triethylamine (84 uL, 0.61 mmol) were added and the mixture was stirred at rt for 1.5 hr. The reaction was quenched with water and the organic layer was separated and dried with sodium sulfate. Removal of solvent gave the crude which was chromatographed on an ISCO machine (0-10% EtOAc/CH2Cl2) to give a white solid. 58 mg.

Workup

  1. customThe reaction was quenched with water
  2. customthe organic layer was separated
  3. dry with materialdried with sodium sulfate
  4. customRemoval of solvent
  5. customgave the crude which
  6. customwas chromatographed on an ISCO machine (0-10% EtOAc/CH2Cl2)
  7. customto give a white solid

Sources & evidence

ORD record
ord-fa55341e9e8949198584807d8f0b3f5f
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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