Hydrochloric Acid → HCID 178431674, compound

HRID 339859Notes

Reaction equation

HRID 339859 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([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:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([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][OH:27])=[N:17][S:16]2(=[O:42])=[O:41])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178431690HCID 178431690, compound

Product 1

HCID 178431674HCID 178431674, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To detach the protecting group, 220 mg of [5-(3-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 4 ml of methanol and, after addition of 0.4 ml of concentrated hydrochloric acid, stirred at room temperature for 1.75 hours. The reaction solution was concentrated by rotary evaporation and coevaporated twice more with 10 ml of toluene, and the residue was purified in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined, the acetonitrile was removed under reduced pressure, and the aqueous residue was basified with saturated aqueous sodium hydrogencarbonate solution. Subsequently, this aqueous residue was extracted with dichloromethane, and the combined organic phases were dried using a phase separator cartridge (Chromabond® PTS) and concentrated by rotary evaporation. The residue was taken up again in a mixture of acetonitrile and water and lyophilized. This gave the product (129 mg) with a molecular weight of 494.6 g/mol (C27H30N2O5S); MS (ESI): m/e=495 (M+H+).

Workup

  1. concentrationThe reaction solution was concentrated by rotary evaporation
  2. customthe residue was purified in a purification laboratory by means of preparative HPLC
  3. customthe acetonitrile was removed under reduced pressure
  4. extractionSubsequently, this aqueous residue was extracted with dichloromethane
  5. customthe combined organic phases were dried
  6. concentrationconcentrated by rotary evaporation
  7. additionThe residue was taken up again in a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-b29d17404f6f4421949bb85e14fd208e
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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