Leucine, N-carboxy-, N-benzyl ester, L- → HCID 131721394, compound

HRID 1737845Notes

Reaction equation

HRID 1737845 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[CH2:13][CH2:12][CH2:11][CH2:10][C@H:2]1[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[NH:24]([C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[C@H:25]([C:30]([OH:32])=O)[CH2:26][CH:27]([CH3:29])[CH3:28]>CCOC(C)=O.[Pd]>[NH:24]([C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[C@H:25]([C:30]([N:1]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:2]1[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[O:32])[CH2:26][CH:27]([CH3:28])[CH3:29]

Participants

5

Reactant 2

HCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 1512714HCID 1512714, compound

Product 1

HCID 131721394HCID 131721394, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of CBZ-L-Pip-OtBu (0.52 g, 1.6 mmol) and Pd on C (10%, 0.10g) in EtOAc was stirred under a hydrogen atmosphere (balloon) for 1h. The reaction mixture was filtered through Celite, and the filtrate was concentrated. The resulting oil was coupled with CBZ-L-Leu (0.43 g, 1.6 mmol) using the procedure described in Example 1 for the preparation of ethyl-3-[BOC-L-N-Me-Phe-L-(Tr-Gln)]-E-propenoate, to provide CBZ-L-Leu-L-Pip-OtBu (0.57 g, 83%) as a colorless oil after column chromatography on silica (20% EtOAc/hexanes): IR (thin film) 3300, 1726, 1642 cm-1 ; 1H NMR (CDCl3) δ 0.93 (d, 3H, J=6.5 Hz), 1.03 (d, 3H, J=6.5 Hz), 1.46 (s, 9H), 1.50-1.60 (m, 2H), 1.64-1.83 (m, 2H), 2.23-2.27 (m, 2H), 3.19-3.28 (m, 2H), 3.77-3.81 (m, 2H), 4.76-4.83 (m, 2H), 5.10 (s, 2H), 5.26 (d, 1H, J=4.7 Hz), 5.60 (d, 1H, J=8.7 Hz), 7.27-7.36 (m, 5H); Anal. (C24H36N2O5) C, H, N.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-83cc2278fde446debbf805f3ab9aa921
Source dataset
uspto-grants-1999_10
Patent number
US05962487

Reaction notes

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