HCID 23533837, compound → HCID 12148457, compound

HRID 276723Notes

Reaction equation

HRID 276723 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH2:13][O:14][CH2:15][C@@H:16]([NH:19][C:20](=[O:38])[C@H:21]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=2)[NH:22]C(OC(C)(C)C)=O)[C:17]#[N:18])[CH:10]=[CH:11][CH:12]=1)=[O:6])[CH:2]=[CH2:3]>C(O)=O>[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH2:13][O:14][CH2:15][C@@H:16]([NH:19][C:20](=[O:38])[C@H:21]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=2)[NH2:22])[C:17]#[N:18])[CH:10]=[CH:11][CH:12]=1)=[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

A solution of N-[2-[(3-(allyloxycarbonyl)-phenyl)methoxy]-1(S)-cyanoethyl]-3-methyl-Nα-(t-butoxycarbonyl)-L-phenylalaninamide (3.18 g, 6.10 mmol) in 96% formic acid (40 mL) is stirred at room temperature for 5.5 hours. Formic acid is evaporated (high vacuum, 25° C.), and the residue is taken up in water (50 mL) and basified with saturated NaHCO3 (100 mL). The resulting mixture is extracted with EtOAc (3×50 mL), and then washed with water (2×100 mL) and brine (1×100 mL), dried over MgSO4, and evaporated to yield N-[2-[(3-(allyloxycarbonyl)-phenyl)methoxy]-1(S)-cyanoethyl]-3-methyl-L-phenylalaninamide as a clear thick oil.

Workup

  1. customFormic acid is evaporated (high vacuum, 25° C.)
  2. extractionThe resulting mixture is extracted with EtOAc (3×50 mL)
  3. washwashed with water (2×100 mL) and brine (1×100 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-d734645a78714fbdafb802923d36cf4a
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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