Trifluoroacetic acid → (S)-2-Amino-3-cyclohexyl-N-((1R,2S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-propionamide trifluoroacetate

HRID 1943306Notes

Reaction equation

HRID 1943306 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C(OC(=O)[NH:14][C@H:15]([C:23](=[O:35])[NH:24][C@H:25]1[CH2:30][C@@H:29]2[C:31]([CH3:33])([CH3:32])[C@@:26]1([CH3:34])[CH2:27][CH2:28]2)[CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)(C)(C)C>C(Cl)Cl>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[NH2:14][C@@H:15]([CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)[C:23]([NH:24][C@H:25]1[CH2:30][C@@H:29]2[C:31]([CH3:33])([CH3:32])[C@@:26]1([CH3:34])[CH2:27][CH2:28]2)=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131730275tert-butyl[(S)-2-cyclohexyl-1-((1R,2S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-ylcarbamoyl)-ethyl]-carbamate

Product 1

HCID 68549461(S)-2-Amino-3-cyclohexyl-N-((1R,2S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-propionamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 ml of TFA were slowly added to a solution of 6.5 g of tert-butyl[(S)-2-cyclohexyl-1-((1R,2S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-ylcarbamoyl)-ethyl]-carbamate (16.0 mmol) in 50 ml of CH2Cl2 at 0° C. under argon. The mixture was allowed to reach RT. After 3 h, the reaction mixture was concentrated. The title compound was obtained as a pale yellow oil which was employed directly in the next step. LC-MS Rt(min) 1.60; calc.: [M+H]+ 307.27 found: 307.39 (method C).

Workup

  1. customto reach RT
  2. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-dc0c5394ee604f5bb3bf9aec8a25cd6f
Source dataset
uspto-grants-2013_03
Patent number
US08389764B2

Reaction notes

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