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

HRID 338134Notes

Reaction equation

HRID 338134 reaction equation
[C:1]([NH:9][C:10]1[S:11][CH2:12][C@@H:13]2[CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][C@:14]2([C:26]2[S:30][N:29]=[CH:28][CH:27]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C[C@@H]2[C@@](C3SC=C(Br)C=3)(N=C(NC(=O)C3C=CC=CC=3)SC2)C1)C=C.FC(F)(F)C(O)=O>ClCCl>[S:30]1[C:26]([C@:14]23[CH2:16][NH:17][CH2:18][C@H:13]2[CH2:12][S:11][C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:15]3)=[CH:27][CH:28]=[N:29]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 86762226tert-butyl (4aR,7aR)-2-benzamido-7a-isothiazol-5-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylateHCID 86762227N-[(4aR,7aR)-6-Allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Product 1

HCID 86762225N-[(4aR,7aR)-7a-Isothiazol-5-yl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of tert-butyl (4aR,7aR)-2-benzamido-7a-isothiazol-5-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate, isomer 2 (1.26 g, 2.83 mmol) in dichloromethane (25 mL) is added trifluoroacetic acid (4.29 mL, 56.68 mmol) drop wise. The resultant solution is stirred for 18 hours at ambient temperature. The solvent is removed under vacuum. The mixture is diluted with ethyl acetate followed by saturated sodium bicarbonate. The layers are separated and the aqueous phase is re-extracted with ethyl acetate (3×). The combined organic layers are dried over sodium sulfate and the solvent is removed under vacuum to give the title compound (850 mg, 2.46 mmol, 87%). ES/MS (m/e): 345 (M+H).

Workup

  1. customThe solvent is removed under vacuum
  2. additionThe mixture is diluted with ethyl acetate
  3. customThe layers are separated
  4. extractionthe aqueous phase is re-extracted with ethyl acetate (3×)
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. customthe solvent is removed under vacuum

Sources & evidence

ORD record
ord-299511b9e9214205b23f9ff505fafabd
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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