Triethylamine → HCID 57999634, compound

HRID 600314Notes

Reaction equation

HRID 600314 reaction equation
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[NH2:19][C@@H:20]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)[C:21]#[N:22].[C:36]([O:40][C:41]([N:43]1[CH2:50][CH2:49][CH2:48][C@H:44]1[C:45](O)=[O:46])=[O:42])([CH3:39])([CH3:38])[CH3:37].C(N(CC)CC)C>CN(C=O)C.O>[C:27]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:29][C:24]([CH2:23][C@H:20]([NH:19][C:45]([C@@H:44]2[CH2:48][CH2:49][CH2:50][N:43]2[C:41]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:42])=[O:46])[C:21]#[N:22])=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 111923Propylphosphonic anhydrideHCID 67269066HCID 67269066, compound

Product 1

HCID 57999634HCID 57999634, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A solution of propane phosphonic acid anhydride (T3P, 50% in DMF, 344 mg) was added to a stirred solution of (S)-2-amino-3-(biphenyl-4-yl)propanenitrile (100 mg), N-tert-butoxycarbonyl-(L)-proline (107 mg) and triethylamine (0.314 mL) in DMF (3 mL) at 20° C. The resulting solution was stirred at 20° C. for 1 hour. Water (15 mL) was added and the mixture extracted with ethyl acetate (3×5 mL). The organics were washed with saturated brine (5×5 mL), dried over sodium sulfate and evaporated to afford the subtitle compound (178 mg).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×5 mL)
  2. washThe organics were washed with saturated brine (5×5 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-89687299853b4348a78e6145143da6ae
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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