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

HRID 1802123Notes

Reaction equation

HRID 1802123 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, 1011), 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-03e3a20e3efe41c7898e3e2831dc642b
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

Loading…