Benzyloxycarbonyl-L-phenylalanine → Alanine, N-benzyloxycarbonyl-3-phenyl-, cyanomethyl ester, L-

HRID 1196811Notes

Reaction equation

HRID 1196811 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[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.[NH:23](C(OCC1C=CC=CC=1)=O)[C@@H:24](C(O)=O)[CH2:25]C1C=CC=CC=1>C(N(CC)CC)C.ClCC#N>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([O:12][CH2:25][C:24]#[N:23])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 675678N-(Benzyloxycarbonyl)-D-phenylalanine

Product 1

HCID 24313Alanine, N-benzyloxycarbonyl-3-phenyl-, cyanomethyl ester, L-

Reagents, catalysts & solvents 2

HCID 7856ChloroacetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

1 gram of Z-L-Phe-OH or Z-D-Phe-OH was dissolved in 2 mL of triethylamine and 2 mL of chloroacetonitrile. The reaction was stirred for two hours at room temperature. The reaction was concentrated under vacuum and the residue taken up in 5 mL ethyl acetate. The ethyl acetate was then washed with 2% Na2CO3 (3x), water (2x), 1 N HCl (2x), water (2x), and 0.5 M or higher saline (1x). The organic phase was dried over MgSO4, and concentrated to dryness. The residue was recrystallized from CH2Cl2 /hexanes. Yield for Z-L-Phe-OCH2CN was 1.0 g (89%). M.P. 53°-55° C. [α]d (c 2, DMF)+6.6°. 1H-NMR (CDCl3) 3.1 (d, 2H, Phe βH), 4.7 (m, 3H, αH and cyanomethyl), 5.1 (s, 2H, CBZ βH), 5.2 (d, 1H, amide), 7.3 (m, 10 H, Phe and CBZ phenyl). Z-D-Phe-OCH2CH, yield 0.88 g (78%). M.P. 53°-54° C. [α]d (c, 2, DMF)-6.1°.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. washThe ethyl acetate was then washed with 2% Na2CO3 (3x), water (2x), 1 N HCl (2x), water (2x), and 0.5 M or higher saline (1x)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated to dryness
  5. customThe residue was recrystallized from CH2Cl2 /hexanes

Sources & evidence

ORD record
ord-940856481a914723a6947266f1ae57aa
Source dataset
uspto-grants-1992_05
Patent number
US05116741

Reaction notes

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