Hydrochloric Acid → methyl (1S)-1-({[(1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentyl]amino}carbonyl)-2,2-dimethylpropylcarbamate

HRID 1174136Notes

Reaction equation

HRID 1174136 reaction equation
[CH2:1]([C@H:8]([NH:28][C:29]([C@@H:31]([NH:36][C:37](=[O:40])[O:38][CH3:39])[C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@@H:9]([OH:27])[CH2:10][C@@H:11]([NH:19]C(OC(C)(C)C)=O)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>C1COCC1>[NH2:19][C@@H:11]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:10][C@H:9]([OH:27])[C@@H:8]([NH:28][C:29]([C@@H:31]([NH:36][C:37](=[O:40])[O:38][CH3:39])[C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86726172methyl (1S)-1-[({(1S,2S,4S)-1-benzyl-4-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate

Product 1

HCID 86726171methyl (1S)-1-({[(1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentyl]amino}carbonyl)-2,2-dimethylpropylcarbamateYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution containing the product from Example 8A (16.97 g, 30.6 mmol) in THF (150 mL) was treated with HCl solution (50 mL, 4 N in dioxane), stirred at 60° C. for 2 hours, cooled and adjusted to pH 8 with 10% NaOH solution. The reaction mixture was partitioned between ethyl acetate and water, and the organic phase was washed with brine and concentrated to give the title compound (13.74 g).

Workup

  1. temperaturecooled
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washthe organic phase was washed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c99d9a2d18fe4384ba743439413fb374
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

Loading…