Boc-orn(boc)-OH → N,N'-bis-BOC-Ornithine tert-Butyl Ester

HRID 1450722Notes

Reaction equation

HRID 1450722 reaction equation
[C:1]([NH:8][C@H:9]([C:21]([OH:23])=[O:22])[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>C(Cl)(Cl)Cl>[C:4]([O:22][C:21](=[O:23])[C@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

3

Reactant 1

HCID 7015803Boc-orn(boc)-OH

Product 1

HCID 10023186N,N'-bis-BOC-Ornithine tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N,N'-bis-BOC-Ornithine tert-Butyl Ester (22) was synthesized from N,N'-bis-BOC-ornithine (12) according to the general procedure : yield, 86%; mp 80°-82° C.; [α]25D+11.3° (c 1.3, CHCl3); 1H NMR δ 5.07 (br d, 1H, J=7.8), 4.63 (m, 1H), 4.16 (t, 1H, J=6.9), 3.14 (t, 2H, J=6.0), 1.82-150 (m, 4H), 1 .45 (s, 9H), 1.43 (s, 18H). Anal. Calcd for C19H36N2O6 : C, 58.7; H, 9.3,; N, 7.2. Found: C, 58.7; H, 9.7; N, 7.2.

Workup

  1. customyield

Sources & evidence

ORD record
ord-7d516d799d8f4e12bb92cfb7cd28707b
Source dataset
uspto-grants-1997_02
Patent number
US05602264

Reaction notes

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