4-Methylmorpholine → HCID 86596971, compound

HRID 2225296Notes

Reaction equation

HRID 2225296 reaction equation
[C:1]([C@H:4]1[C@@H:9]([NH2:10])[CH2:8][CH2:7][C@@H:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5]1)(=[O:3])[CH3:2].[F:19][C:20]([F:35])([F:34])[C:21]1[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=1)[C:24]([NH:26][CH2:27][C:28](O)=[O:29])=[O:25].CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[C:1]([C@H:4]1[C@@H:9]([NH:10][C:28](=[O:29])[CH2:27][NH:26][C:24](=[O:25])[C:23]2[CH:31]=[CH:32][CH:33]=[C:21]([C:20]([F:19])([F:35])[F:34])[CH:22]=2)[CH2:8][CH2:7][C@@H:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2777432((3-(Trifluoromethyl)benzoyl)amino)acetic acidHCID 86596970HCID 86596970, compound

Product 1

HCID 86596971HCID 86596971, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tert-butyl (1R,3R,4S)-3-acetyl-4-aminocyclohexylcarbamate (500 mg) dissolved in DMF (2 mL) prior to the addition of 2-(3-(trifluoromethyl)benzamido)acetic acid (626 mg), 4-methylmorpholine (1.1 mL), and BOP (1.3 g). The reaction was stirred for 12 h at rt and then partitioned between EtOAc and 1N HCl solution. The organic phases were combined, washed with saturated NaHCO3 and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography to afford tert-butyl (1R,3R,4S)-3-acetyl-4-(2-(3-(trifluoromethyl)benzamido)acetamido)cyclohexylcarbamate (430 mg). MS found: (M+H)+=486.2.

Workup

  1. custompartitioned between EtOAc and 1N HCl solution
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7ac7c3ad5ab142cabbca1360a050ed4d
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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