HCID 480330, compound → HCID 480337, compound

HRID 1167265Notes

Reaction equation

HRID 1167265 reaction equation
[O:1]1[CH2:6][CH:5]([O:7][C:8](=[O:47])[NH:9][C@@H:10]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@H:11]([OH:39])[CH2:12][N:13]([CH2:31][C:32]([CH3:38])([CH3:37])[CH2:33][CH2:34][C:35]#[N:36])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23]CC3C=CC=CC=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:4][O:3][CH2:2]1>CO>[O:1]1[CH2:6][CH:5]([O:7][C:8](=[O:47])[NH:9][C@@H:10]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@H:11]([OH:39])[CH2:12][N:13]([CH2:31][C:32]([CH3:38])([CH3:37])[CH2:33][CH2:34][C:35]#[N:36])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:4][O:3][CH2:2]1

Participants

3

Reactant 1

HCID 480330HCID 480330, compound

Product 1

HCID 480337HCID 480337, compoundYield 115.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{(1S,2R)-1-Benzyl-3-[(4-cyano-2,2-dimethyl-butyl)-(4-benzyloxybenzenesulfonyl)-amino]-2-hydroxy-propyl]-carbamic acid[1,3]dioxan-5-yl ester (2.2 mg, 0.003 mmol) was dissolved in methanol (1 mL). Solution was degassed with nitrogen for 5 minutes the 10% Pd/C (2 mg) was added. Reaction was pressurized with H2 (1 ATM) and stirred for 30 minutes. Catalyst removed by filtration and solvent was removed in vacuo leaving 2.0 mg (95%) of product as a colorless residue. MS(ES): 576.2 (M+1), HPLC; tR=10.39 min. (84%).

Workup

  1. customSolution was degassed with nitrogen for 5 minutes the 10% Pd/C (2 mg)
  2. additionwas added
  3. customReaction
  4. customCatalyst removed by filtration and solvent
  5. customwas removed in vacuo

Sources & evidence

ORD record
ord-aa0ddf707cd84385ae2f0521b3b86cfe
Source dataset
uspto-grants-2003_09
Patent number
US06617350B2

Reaction notes

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