Acetic Anhydride → HCID 178475103, compound

HRID 1361340Notes

Reaction equation

HRID 1361340 reaction equation
[OH:1][C:2]([C:4](F)(F)F)=O.[NH2:8][C:9](=[NH:42])[N:10]1[CH2:14][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C@H:12]([C:22]([N:24]2[CH2:28][CH2:27][C@H:26]([N:29]([C@H:35]3[CH2:40][CH2:39][C@@H:38]([CH3:41])[CH2:37][CH2:36]3)[C:30](=[O:34])[CH:31]([CH3:33])[CH3:32])[CH2:25]2)=[O:23])[CH2:11]1.C(OC(=O)C)(=O)C>C(Cl)Cl>[C:2]([NH:42][C:9](=[NH:8])[N:10]1[CH2:14][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C@H:12]([C:22]([N:24]2[CH2:28][CH2:27][C@H:26]([N:29]([C@H:35]3[CH2:36][CH2:37][C@@H:38]([CH3:41])[CH2:39][CH2:40]3)[C:30](=[O:34])[CH:31]([CH3:33])[CH3:32])[CH2:25]2)=[O:23])[CH2:11]1)(=[O:1])[CH3:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178454576HCID 178454576, compound

Product 1

HCID 178475103HCID 178475103, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(3S)-1-{[(3S,4R)-1-[amino(imino)methyl]-4-(4-chlorophenyl)pyrrolidine-3-yl]carbonyl}pyrrolidine-3-yl]-2-methyl-N-(cis-4-methylcyclohexyl)propaneamide TFA salt (185 mg, 0.3 mmol) prepared in Example E9 in DCM (3 ml) was added acetic acid anhydride (46 mg, 0.45 mmol) and TEA (71 mg, 0.7 mmol), and stirred at rt for 6 h. After the reaction finished, the solvent was concentrated in vacuo, extracted with water and EtOAc, and the organic layer was dried over MgSO4. The organic solution was concentrated in vacuo, and purified by HPLC to give the title compound (139 mg, 85%).

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. extractionextracted with water and EtOAc
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationThe organic solution was concentrated in vacuo
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-4e55dc08860c4fdaa16b4f200a9a997b
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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