HCID 23533837, compound → HCID 12148457, compound

HRID 2414390Notes

Reaction equation

HRID 2414390 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH:36]=[CH:37][CH:38]=1)[CH2:10][O:11][CH2:12][C@@H:13]([NH:16][C:17](=[O:35])[C@H:18]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=1)[NH:19]C(OC(C)(C)C)=O)[C:14]#[N:15])=[O:6])[CH:2]=[CH2:3]>C(O)=O>[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH:36]=[CH:37][CH:38]=1)[CH2:10][O:11][CH2:12][C@@H:13]([NH:16][C:17](=[O:35])[C@H:18]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=1)[NH2:19])[C:14]#[N:15])=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 23533837HCID 23533837, compound

Product 1

HCID 12148457HCID 12148457, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

N-[2-[3-(allyloxycarbonyl)-benzyloxy]-1(S)-cyanoethyl]-3-methyl-Nα-(t-butoxycarbonyl)-L-phenylalaninamide (4.36 g, 8.37 mmol) in formic acid (47 mL) is stirred at room temp. for 6 h, after which time the formic acid is evaporated at 25° C. The residue is then dissolved in water (50 mL), basified with sat'd aqueous NaHCO3, and extracted with ethyl acetate (3×50 mL). The combined organic layers are then washed with water (50 mL), brine (50 mL), dried (MgSO4) and evaporated to yield N-[2-[3-(allyloxycarbonyl)-benzyloxy]-1(S)-cyanoethyl]-3-methyl-L-phenylalaninamide, as a clear oil, which is utilized without further purification.

Workup

  1. customafter which time the formic acid is evaporated at 25° C
  2. dissolutionThe residue is then dissolved in water (50 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers are then washed with water (50 mL), brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-eaeaa65bdc084c3b9cb1a8ba9c6f6b93
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

Loading…