Ammonia → HCID 91026852, compound

HRID 852873Notes

Reaction equation

HRID 852873 reaction equation
CC[N:3](C(C)C)C(C)C.[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C@@H:25]([NH:31][C:32](=[O:45])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:26][CH2:27][C:28](O)=[O:29])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N>CN(C=O)C>[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C@@H:25]([NH:31][C:32](=[O:45])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:26][CH2:27][C:28](=[O:29])[NH2:3])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 446400(4S)-5-[4-(Benzyloxy)phenyl]-4-(7-phenylheptanamido)pentanoic acid

Product 1

HCID 91026852HCID 91026852, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (0.12 mL, 0.68 mmol) was added dropwise to a stirred solution of (63) (300 mg, 0.62 mmol) and BOP (300 mg, 0.68 mmol) in DMF (4 mL). After 10 min, NH3 solution (25%, 0.75 mL) was added, and the mixture stirred for 1 h. The solvent was removed under reduced pressure, and the crude residue diluted with water and extracted into warm EtOAc. The combined extracts were then washed with HCl solution (1 M), water, saturated NaHCO3 solution, brine and dried over MgSO4. Evaporation of the solvent in vacuo gave (64) (300 mg, quantitative) as a white powder, ESMS 487 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe crude residue diluted with water
  3. extractionextracted
  4. temperatureinto warm EtOAc
  5. washThe combined extracts were then washed with HCl solution (1 M), water, saturated NaHCO3 solution, brine
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-0f77fc726ff044d49c5a7ece3ed2780b
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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