Hydrochloric Acid → N-[(4aR,7aR)-7a-Isothiazol-5-yl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide hydrochloride

HRID 338135Notes

Reaction equation

HRID 338135 reaction equation
[ClH:1].[C:2]([NH:10][C:11]1[S:12][CH2:13][C@@H:14]2[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][C@:15]2([C:27]2[S:31][N:30]=[CH:29][CH:28]=2)[N:16]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CC(O)C.CC(OC)(C)C>[ClH:1].[S:31]1[C:27]([C@:15]23[CH2:17][NH:18][CH2:19][C@H:14]2[CH2:13][S:12][C:11]([NH:10][C:2](=[O:9])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:16]3)=[CH:28][CH:29]=[N:30]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86762226tert-butyl (4aR,7aR)-2-benzamido-7a-isothiazol-5-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Product 1

HCID 86762228N-[(4aR,7aR)-7a-Isothiazol-5-yl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide hydrochlorideYield 98%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

Hydrogen chloride 6 M in 2-propanol (1.65 L, 9.9 mol) is added to tert-butyl (4aR,7aR)-2-benzamido-7a-isothiazol-5-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (200 g, 449.9 mol) in 2-propanol (1.6 L) at 22° C. and stirred for 18 hours. The mixture is concentrated to give a white solid. The solid is diluted with MTBE (1 L), stirred at 22° C. for 1 hour, filtered and dried under vacuum to constant weight to give the title compound (170 g, 98%). ES/MS (m/e): 345.0 (M+H).

Workup

  1. concentrationThe mixture is concentrated
  2. customto give a white solid
  3. stirringstirred at 22° C. for 1 hour
  4. filtrationfiltered
  5. customdried under vacuum to constant weight

Sources & evidence

ORD record
ord-2ecd7b4fdb77492986c338d72a4b2e28
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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