Hydrochloric Acid → (S)-2-amino-3-hydroxy-N-{2-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]ethyl}propionamide

HRID 1401866Notes

Reaction equation

HRID 1401866 reaction equation
Cl.C(OC(=O)[NH:8][C@H:9]([C:12](=[O:35])[NH:13][CH2:14][CH2:15][C:16]1[S:17][CH:18]=[C:19]([C:21]2[CH:30]=[CH:29][C:28]3[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:34])([CH3:33])[C:23]=3[CH:22]=2)[N:20]=1)[CH2:10][OH:11])(C)(C)C>O1CCOCC1>[NH2:8][C@@H:9]([CH2:10][OH:11])[C:12]([NH:13][CH2:14][CH2:15][C:16]1[S:17][CH:18]=[C:19]([C:21]2[CH:30]=[CH:29][C:28]3[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:34])([CH3:33])[C:23]=3[CH:22]=2)[N:20]=1)=[O:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67324809((S)-2-hydroxy-1-{2-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]ethylcarbamoyl}ethyl)carbamic acid tert-butyl ester

Product 1

HCID 67322250(S)-2-amino-3-hydroxy-N-{2-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]ethyl}propionamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The protecting group is cleaved off as already described using HCl in dioxane starting from 82 mg (0.16 mmol) of ((S)-2-hydroxy-1-{2-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]ethylcarbamoyl}ethyl)carbamic acid tert-butyl ester from step c. The product is purified by means of preparative HPLC and is in the form of the formate.

Workup

  1. customThe product is purified by means of preparative HPLC

Sources & evidence

ORD record
ord-b8317bcc5a754a2589d1ad8df4e5e953
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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