N-carbobenzyloxyalanine → HCID 9966575, compound

HRID 1450725Notes

Reaction equation

HRID 1450725 reaction equation
[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[C@H:2]([C:4]([OH:6])=[O:5])[CH3:3]>C1COCC1>[CH2:10]([O:5][C:4](=[O:6])[C@H:2]([CH3:3])[NH:1][C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 736104N-carbobenzyloxyalanine

Product 1

HCID 9966575HCID 9966575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

CBZ-Ala (10, 0.825 g, 0.0037 mol) was added to a solution of 2 (R=Bn, 2.8 g, 200 mol %) in 15 mL of THF. The reaction was heated at 45° C. for 20 h, after which the reaction was cooled, evaporated and following the general procedure gave 16 as a clear oil, 1.07 g, 92%: [α]25D -31.7° (c 1.1, EtOH); IR 3340, 3060, 3030, 1720; 1H NMR δ 7.45-7.28 (m, 10H), 5.43 (d, 1H, J=7), 5.15-5.08 (m, 4H), 4.43-4.40 (m, 1H), 1.38 (d, 3H, J=7.1). Anal. Calcd for C18H19NO4 : C, 69.0; H, 6.1,; N, 4.5. Found: C, 69.3; H, 6.2; N, 4.7.

Workup

  1. temperatureafter which the reaction was cooled
  2. customevaporated

Sources & evidence

ORD record
ord-8c54daeb330c44f3966ab8104adcd52e
Source dataset
uspto-grants-1997_02
Patent number
US05602264

Reaction notes

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