Dimethylformamide → HCID 131723196, compound

HRID 843389Notes

Reaction equation

HRID 843389 reaction equation
Cl.[NH2:2][C@H:3]([CH3:15])[C:4]([NH:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2N=N1.CCN([CH:49]([CH3:51])[CH3:50])C(C)C.CN([CH:55]=[O:56])C>>[C:26]1([CH:51]([CH2:49][CH3:50])[C:55]([NH:2][C@H:3]([CH3:15])[C:4]([NH:6][O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])=[O:56])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 88035642HCID 88035642, compound

Product 1

HCID 131723196HCID 131723196, compoundYield 88%

Procedure

To a solution of 2-amino-N-benzyloxy-(R)-propionamide HCl Salt (200 mg, 0.868 mmol) and (R,S)-2-phenylbutyric acid (143 mg, 0.868 mmol) in 3 mL DMF cooled in an ice bath was added BOP (384 mg, 0.868 mmol) followed by DIEA (0.7 mL, 4 mmol). After stirring for 1 hour at room temperature, the solution was diluted with EtOAC, washed with NaHCO3 and brine, dried over MgSO4, and concentrated. Purification on a silica gel column using 5% MeOH in CH2Cl2 gave the amide product (260 mg, 88%) as a solid. MS (ESI): (M−H)−=339.1.

Workup

  1. additionthe solution was diluted with EtOAC
  2. washwashed with NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification on a silica gel column

Sources & evidence

ORD record
ord-f27406059d3540a5ae4270e8594f7985
Source dataset
uspto-grants-2002_04
Patent number
US06376665B1

Reaction notes

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