Hydrochloric Acid → HCID 69358356, compound

HRID 852612Notes

Reaction equation

[O:1]=[S:2]1(=[O:28])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11][N:12]2C(OC(C)(C)C)=O.CCOCC.[ClH:34]>>[ClH:34].[O:28]=[S:2]1(=[O:1])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11][NH:12]2

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 3283Diethyl Ether

HCID 69359816HCID 69359816, compound

Product 1

HCID 69358356HCID 69358356, compoundYield 100%

Procedure

1-(1,1-Dimethylethyl) 6-methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-2,3-dihydro-1H-indole-1,6-dicarboxylate (D233) (500 mg, 1.2 mmol, 1 equiv) was dissolved in a 4N HCl solution in Et2O (10 ml, 40 mmol, excess) and the resulting solution was stirred at room temperature for 1 h then concentrated in vacuo. Trituration of the residue with Et2O gave methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-2,3-dihydro-1H-indole-6-carboxylate hydrochloride salt (D234) (430 mg, 100%) as a white solid which was used in the next step without further purification. [M+H]+=311.0, RT=2.16 min.

Workup

concentrationthen concentrated in vacuo

Sources & evidence

ORD record: ord-a0939ffaab3141dcb18a3b8dc081c0be
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253198B2

Reaction notes

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