Ethyl Acetate → HCID 71568990, compound

HRID 714768Notes

Reaction equation

HRID 714768 reaction equation
Cl.[Si:2]([O:19][C@H:20]([C:27]1[S:28][CH:29]=[CH:30][N:31]=1)[C@H:21]1[CH2:26][CH2:25][CH2:24][NH2+:23][CH2:22]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].C(OCC)(=O)C>CO.O>[Si:2]([O:19][C@H:20]([C:27]1[S:28][CH:29]=[CH:30][N:31]=1)[C@H:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 131734069HCID 131734069, compound

Product 1

HCID 71568990HCID 71568990, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

30 ml of hydrogen chloride (4 M in 1,4-dioxane) were added dropwise at +5° C. to a solution of 1.08 g (2.0 mmol) of tert-butyl (S)-3-[(S)-(tert-butyldiphenylsilanyloxy)thiazol-2-ylmethyl]-piperidine-1-carboxylate in 30 ml of dichloromethane. The reaction mixture was stirred at room temperature for 2 hours. Evaporation gave 1.03 g of (S)-3-[(S)-(tert-butyldiphenylsilanyloxy)thiazol-2-yl-methyl]piperidinium hydrochloride; HPLC/MS (M+H)+=437; rotation value in methanol [α]20D=−18.1°. The hydrochloride was dissolved in 10 ml of water, cooled in an ice bath, and 1 ml of sodium hydroxide solution (2 M) was added dropwise. The precipitate was taken up with ethyl acetate, washed with saturated sodium chloride solution, dried over sodium sufate, filtered and evaporated, giving 0.8 g of (S)-3-[(S)-(tert-butyldiphenylsilanyloxy)thiazol-2-ylmethyl]piperidine as amorphous resin; HPLC/MS (M+H)+=437; rotation value in methanol [α]20D=−22.1°. 1H NMR (400 MHz, DMSO) δ 7.69-7.56 (m, 4H), 7.52-7.38 (m, 6H), 7.38-7.26 (m, 2H), 4.84 (d, J=6.6, 1H), 4.03 (q, J=7.1, 1H), 2.94 (d, J=11.2, 1H), 2.73 (d, J=11.8, 1H), 2.25-2.10 (m, 2H), 1.78 (dtd, J=10.5, 6.9, 3.3, 1H), 1.49-1.30 (m, 2H), 1.19-1.10 (m, 2H), 1.04-0.93 (m, 9H).

Workup

  1. temperaturecooled in an ice bath
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over sodium sufate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-941f43c764af4b8c8638a8f023e6a169
Source dataset
uspto-grants-2015_11
Patent number
US09187469B2

Reaction notes

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