Hydrochloric Acid → 2,2-Dimethyl-propionic acid (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propyl ester

HRID 336455Notes

Reaction equation

C(OC([NH:8][C@H:9]([CH2:12][S:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH2:10][OH:11])=O)(C)(C)C.[CH3:23][C:24]([CH3:29])([CH3:28])[C:25](Cl)=[O:26].Cl>>[NH2:8][C@@H:9]([CH2:12][S:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[CH2:10][O:11][C:25](=[O:26])[C:24]([CH3:29])([CH3:28])[CH3:23]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 62493Pivaloyl chloride

HCID 14539894(S)-2-t-butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propanol

Product 1

HCID 595430572,2-Dimethyl-propionic acid (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propyl ester

Procedure

(S)-2-t-butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propanol prepared in Step C, trimethylacetylchloride and HCl (4 N dioxane solution) were reacted according to the same procedures as Steps D and E of Preparation 31 consecutively to give the title compound.

Workup

customaccording to the same procedures as Steps D and E of Preparation 31 consecutively

Sources & evidence

ORD record: ord-6efe245bf46944749700bb6a262b2d43
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889691B2

Reaction notes

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