Hydrochloric Acid → Benzyl((5s)-7-[(3-amino-2-hydroxypropyl)amino]-5-{[(benzyloxy)carbonyl]amino}-7-oxoheptyl)carbamate hydrochloride

HRID 269656Notes

Reaction equation

HRID 269656 reaction equation
[ClH:1].[CH2:2]([O:9][C:10](=[O:44])[NH:11][C@H:12]([CH2:28][C:29]([NH:31][CH2:32][CH:33]([OH:43])[CH2:34][NH:35]C(OC(C)(C)C)=O)=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20]CC1C=CC=CC=1)=[O:19])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[ClH:1].[CH2:2]([N:17]([CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]([NH:11][C:10]([O:9][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:44])[CH2:28][C:29]([NH:31][CH2:32][CH:33]([OH:43])[CH2:34][NH2:35])=[O:30])[C:18](=[O:19])[OH:20])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131727161benzyl{(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[2-({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)-2-oxoethyl]pentyl}carbamate

Product 1

HCID 69219646Benzyl((5s)-7-[(3-amino-2-hydroxypropyl)amino]-5-{[(benzyloxy)carbonyl]amino}-7-oxoheptyl)carbamate hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

11 ml of a 4M solution of hydrogen chloride in dioxane are added to a solution of 160 mg (0.267 mmol) of benzyl{(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[2-({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)-2-oxoethyl]pentyl}carbamate (Example 160A) in 5.5 ml of dioxane at 0° C. The mixture is stirred at RT for 1 h. The reaction solution is concentrated, coevaporated with dichloromethane several times and dried under high vacuum. The crude product is reacted without further purification.

Workup

  1. concentrationThe reaction solution is concentrated
  2. customdried under high vacuum
  3. customThe crude product is reacted without further purification

Sources & evidence

ORD record
ord-3fc73e7a9e9c43728f173b23b7fc075e
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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