HCID 86586953, compound → HCID 21356764, compound

HRID 1167282Notes

Reaction equation

HRID 1167282 reaction equation
[CH2:1]([C@H:8]([NH:23][C:24](=[O:34])[O:25][CH:26]1[CH:33]2[CH:29]([O:30][CH2:31][CH2:32]2)[O:28][CH2:27]1)[C@H:9]([OH:22])[CH2:10][NH:11]C(OCC1C=CC=CC=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[NH2:11][CH2:10][C@@H:9]([OH:22])[C@@H:8]([NH:23][C:24](=[O:34])[O:25][C@@H:26]1[C@H:33]2[C@H:29]([O:30][CH2:31][CH2:32]2)[O:28][CH2:27]1)[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86586953HCID 86586953, compound

Product 1

HCID 21356764HCID 21356764, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 4.0 g (8.5 mmol) of 3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-3-[(benzyloxy)carbonyl]amino-2-hydroxypropyl)carbamate and 0.5 g of 5% Pd(C) in 200 mL of MeOH was subjected to hydrogenation at 45 psi. After 3.5 hours the reaction vessel was purged with nitrogen, catalyst was removed by filtration through celite and the filtrate was concentrated in vacuo to afford 2.72 g (95%) of the desired product as a white solid. NMR (DMSO-d6): 7.23-7.04 (m, 6H), 5.45 (d, 1H), 4.91-4.75 (m, 2H), 3.79 (dd, 1H), 3.68 (t, 1H), 3.53 (m, 3H), 3.21 (m, 2H), 3.01 (dd, 1H), 2.74 (q, 1H), 2.57 (dd, 1H), 2.41 (m, 1H), 1.60-1.28 (m, 3H), 1.22 (dd, 1H). MS(ESI): 337(M+H).

Workup

  1. customAfter 3.5 hours the reaction vessel was purged with nitrogen, catalyst
  2. customwas removed by filtration through celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b359949d1a5f45a5be70fedfb57b5652
Source dataset
uspto-grants-2003_09
Patent number
US06617350B2

Reaction notes

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