Hydrochloric Acid → HCID 131734069, compound

HRID 714767Notes

Reaction equation

HRID 714767 reaction equation
[ClH:1].[Si:2]([O:19][C@H:20]([C:34]1[S:35][CH:36]=[CH:37][N:38]=1)[C@H:21]1[CH2:26][CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[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>ClCCl>[ClH:1].[Si:2]([O:19][C@H:20]([C:34]1[S:35][CH:36]=[CH:37][N:38]=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: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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89585238HCID 89585238, compound

Product 1

HCID 131734069HCID 131734069, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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. customEvaporation

Sources & evidence

ORD record
ord-1764394e7d5640e8acd33cc00b1cdc47
Source dataset
uspto-grants-2015_11
Patent number
US09187469B2

Reaction notes

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