Hydrochloric Acid → Hydrochloric Acid

HRID 2045135Notes

Reaction equation

HRID 2045135 reaction equation
[C:1]([Cl:4])(=O)[CH3:2].Cl.[CH2:6]([O:8][C:9](=[O:28])[C@H:10]([OH:27])[CH2:11][C@H:12]([NH2:26])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[CH3:7]>C(O)CCC>[CH2:6]([O:8][C:9](=[O:28])[C@H:10]([OH:27])[CH2:11][C@H:12]([NH2:26])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:18][CH:19]=1)[CH2:7][CH2:1][CH3:2].[ClH:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 67969400(2R,4R)-4-amino-5-biphenyl-4-yl-2-hydroxypentanoic acid ethyl ester

Product 2

HCID 313Hydrochloric AcidHCID 67969306(2R,4R)-4-Amino-5-biphenyl-4-yl-2-hydroxypentanoic Acid Butyl Ester

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

1-Butanol (40 mL, 400 mmol) was cooled in an ice bath and acetyl chloride was added dropwise until a concentration of 4N HCl was achieved. The mixture was warmed to room temperature. (2R,4R)-4-amino-5-biphenyl-4-yl-2-hydroxypentanoic acid ethyl ester (HCl salt; 250 mg, 710 μmol) was added to the acidified butanol (15 mL) and the mixture was capped and heated to 80° C. for 3 hours. The resulting product was dried under vacuum to yield the title compound as a white/orange flaky solid HCl salt (220 mg).

Workup

  1. customthe mixture was capped
  2. temperatureheated to 80° C. for 3 hours
  3. customThe resulting product was dried under vacuum

Sources & evidence

ORD record
ord-aad2a4f9db21497187bf276add703c52
Source dataset
uspto-grants-2013_11
Patent number
US08586536B2

Reaction notes

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