تفاعل #2364155

ord-02af6a52d476499a9ed93c2b5c070fe8

معادلة التفاعل

CC(C)(C)OC(=O)N(Cc1ccccc1[N+](=O)[O-])[C@H](C(=O)OC1CCCC1)c1ccccc1
mixture
CC(C)(C)OC(=O)N(Cc1ccccc1[N+](=O)[O-])[C@H](C(=O)OC1CCCC1)c1ccccc1
(S)-[tert-Butoxycarbonyl-(2-nitro-benzyl)-amino]-phenyl-acetic acid cyclopentyl ester
NC(=O)[O-]
carbamate
→
CC(C)(C)OC(=O)N(Cc1ccccc1N)[C@H](C(=O)OC1CCCC1)c1ccccc1
solid
CC(C)(C)OC(=O)N(Cc1ccccc1N)[C@H](C(=O)OC1CCCC1)c1ccccc1
(S)-[(2-Amino-benzyl)-tert-butoxycarbonyl-amino]-phenyl-acetic acid cyclopentyl ester

المتفاعلات

CC(C)(C)OC(=O)N(Cc1ccccc1[N+](=O)[O-])[C@H](C(=O)OC1CCCC1)c1ccccc1
mixture
CC(C)(C)OC(=O)N(Cc1ccccc1[N+](=O)[O-])[C@H](C(=O)OC1CCCC1)c1ccccc1
(S)-[tert-Butoxycarbonyl-(2-nitro-benzyl)-amino]-phenyl-acetic acid cyclopentyl ester
NC(=O)[O-]
carbamate

الكواشف

[Pd]
Pd/C

المذيبات

CCOC(C)=O
EtOAc

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحThe Pd/C catalyst was filtered off through a pad of celite
  2. 2
    تركيزThe filtrate was concentrated under reduced pressure

الإجراء التجريبي

A mixture of stage 2 carbamate (4.44 g, 9.78 mmol) and 10% Pd/C (0.7 g) in EtOAc (130 ml) was hydrogenated at room temperature for 18 h under balloon pressure. The Pd/C catalyst was filtered off through a pad of celite. The filtrate was concentrated under reduced pressure to yield a white solid (4.25 g). LCMS purity 100%, m/z 425 [M++H]+,

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09133104B2uspto-grants-2015_09