Hydrochloric Acid → HCID 178431676, compound

HRID 339829Notes

Reaction equation

HRID 339829 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[C:20]([CH3:22])([CH3:21])[O:19][C:18]([NH:23][C@H:24]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:25][CH2:26][O:27][Si](C(C)(C)C)(C)C)=[N:17][S:16]2(=[O:42])=[O:41])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[C:20]([CH3:22])([CH3:21])[O:19][C:18]([NH:23][C@H:24]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:25][CH2:26][OH:27])=[N:17][S:16]2(=[O:41])=[O:42])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178431691HCID 178431691, compound

Product 1

HCID 178431676HCID 178431676, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To detach the protecting group, 40 mg of [5-(4-benzyloxyphenyl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-2-yl]-[(S)-3-(tert-butyldimethylsilanyloxy)-1-phenylpropyl]amine were dissolved in 5 ml of methanol and, after addition of 1 ml of 2 N hydrochloric acid, stirred at room temperature for 1 hour. The reaction solution was neutralized with 2 ml of 1 N aqueous sodium hydroxide solution and concentrated by rotary evaporation, and the residue was purified in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined and lyophilized. This gave the product (19.7 mg) with a molecular weight of 494.6 g/mol (C27H30N2O5S); MS (ESI): m/e=495 (M+H+).

Workup

  1. concentrationconcentrated by rotary evaporation
  2. customthe residue was purified in a purification laboratory by means of preparative HPLC

Sources & evidence

ORD record
ord-86f53c2ddfb34f628bbd17d1a0f2ab00
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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