Hydrochloric Acid → 2-Amino-2-(6-octylbenzo[d]thiazol-2-yl)propan-1-ol

HRID 709907Notes

Reaction equation

HRID 709907 reaction equation
[Si]([O:8][CH2:9][C:10]([NH:29]S(C(C)(C)C)=O)([C:12]1[S:13][C:14]2[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:18]=[CH:17][C:15]=2[N:16]=1)[CH3:11])(C(C)(C)C)(C)C.Cl>CO>[NH2:29][C:10]([C:12]1[S:13][C:14]2[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:18]=[CH:17][C:15]=2[N:16]=1)([CH3:11])[CH2:9][OH:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67409337N-(1-(tert-butyldimethylsilyloxy)-2-(6-octylbenzo[d]thiazol-2-yl)propan-2-yl)-2-methylpropane-2-sulfinamide

Product 1

HCID 686039792-Amino-2-(6-octylbenzo[d]thiazol-2-yl)propan-1-olYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A methanol (5 mL) solution of N-(1-(tert-butyldimethylsilyloxy)-2-(6-octylbenzo[d]thiazol-2-yl)propan-2-yl)-2-methylpropane-2-sulfinamide (90 mg) and 4N HCl (0.325 mL, 1.3 mmol) was stirred at r.t. for 24 h. Then the mixture was extracted with EtOAc and purified by silica gel chromatography using PE/EA (1/2) to give product the title compound (11 mg, 26%). EDI-MS (M+1): 321. 1H NMR (300 MHz, CDCl3) δ 7.840 (d, 1H), 7.699 (s, 1H), 7.276 (d, 1H), 4.031 (d, 1H), 3.722 (d, 1H), 2.730 (t, 2H), 2.632 (b, 3H), 1.666 (t, 2H), 1.564 (s, 3H), 1.330-1.283 (m, 10H), 0.866 (t, 3H). HPLC: 96.9% (214 nm); 98.0% (254 nm).

Workup

  1. extractionThen the mixture was extracted with EtOAc
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-17f18abd91a44c5d8c6a6238ad945b9f
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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