L-Phenylalanine → HCID 54200495, compound

HRID 434412Notes

Reaction equation

HRID 434412 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:20][C:21]([CH3:44])([CH3:43])[C:22](=[O:42])[O:23][CH2:24][O:25][P:26]([CH2:38][C:39](O)=[O:40])([CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:27]>CN(C)C=O>[CH3:20][C:21]([CH3:44])([CH3:43])[C:22](=[O:42])[O:23][CH2:24][O:25][P:26]([CH2:38][C:39]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:40])([CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:27]

Participants

5

Reactant 3

HCID 6140L-PhenylalanineHCID 8471TriethylamineHCID 13187471HCID 13187471, compound

Product 1

HCID 54200495HCID 54200495, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-Phenylalanine (1.65 g, 10 mmol), triethylamine (2.8 ml, 20 mmol) and [[(2,2-dimethyl-1-oxopropoxy)methoxy]-(4-phenylbutyl)phosphinyl]acetic acid, N-hydroxy succinimide ester (4.67 g, 10 mmol) are dissolved in 50 ml of dry dimethylformamide and stirred overnight under argon at room temperature. The reaction mixture is partitioned between dichloromethane and 5% KHSO4, and the organic layer is washed with water and brine and then dried and evaporated to yield the desired product.

Workup

  1. customThe reaction mixture is partitioned between dichloromethane and 5% KHSO4
  2. washthe organic layer is washed with water and brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-e531b3f251a348da801a2f9d514761b8
Source dataset
uspto-grants-1983_08
Patent number
US04396772

Reaction notes

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