HCID 86586953, compound → HCID 21356764, compound

HRID 429980Notes

Reaction equation

HRID 429980 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-e20842b22d354d0781f0b7cf7211dfe4
Source dataset
uspto-grants-2001_11
Patent number
US06319946B1

Reaction notes

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