Diisopropylethylamine → HCID 69883297, compound

HRID 843398Notes

Reaction equation

HRID 843398 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:28][NH:29][C@@H:30]([C:32]([O:34][CH3:35])=[O:33])[CH3:31].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:28][N:29]([C@H:30]([CH3:31])[C:32]([O:34][CH3:35])=[O:33])[C:10](=[O:12])[CH:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[CH2:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 60149789(R)-Methyl 2-(methylamino)propanoate hydrochlorideHCID 69950176HCID 69950176, compound

Product 1

HCID 69883297HCID 69883297, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R/S)-α-t-butoxycarbonylmethyl-4-benzyloxyphenylacetic acid 48b (4.8 g, 13.48 mmol) and methyl N-methyl-D-alaninate hydrochloride (2.9 g, 18.9 mmol) in DMF (30 mL) cooled in an ice bath was added BOP (6.56 g, 14.83 mmol) followed by DIEA (16.5 mL, 94.5 mmol) and the solution was stirred overnight. EtOAc was added and the solution was washed with NaHCO3 and brine, dried over MgSO4, and concentrated. The residue was purified on a silica gel column by eluting with 40% EtOAc/hexane to give the desired product (3.0 g, 49%) as a solid. MS (CI—NH3): (M+H)+=456.

Workup

  1. washthe solution was washed with NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column
  5. washby eluting with 40% EtOAc/hexane

Sources & evidence

ORD record
ord-ebe1d8d9d8794fe3ac5c2fee7ffd080e
Source dataset
uspto-grants-2002_04
Patent number
US06376665B1

Reaction notes

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