Sodium Sulfite → (S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetic acid

HRID 510261Notes

Reaction equation

HRID 510261 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:19][OH:20])[C:8]([CH3:26])=[CH:7][C:5]=2[N:6]=1.[O-:27]S([O-])=O.[Na+].[Na+]>C(#N)C.O.CCOC(C)=O>[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=3)=[C:9]([C@H:18]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[C:19]([OH:27])=[O:20])[C:8]([CH3:26])=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 2

HCID 24437Sodium SulfiteHCID 86699791(S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol

Product 1

HCID 86699792(S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol (1.95 g, 5.00 mmol) in acetonitrile (25 mL) and water (1 mL) was added H5IO6 (1.37 g, 6.00 mmol) and CrO3 (1.00 g, 10.0 mmol). The mixture was stirred at rt for 1 h and was diluted with EtOAc (50 mL) and a saturated solution of Na2SO3 (50 mL). The layers were separated, and the aqueous layer was extracted with EtOAc. The crude material was taken on without further purification. 1H-NMR: 400 MHz, (CDCl3) δ: 7.42-7.61 (m, 4H), 7.20 (s, 1H), 5.11 (s, 1H), 2.47 (s, 3H), 0.93 (s, 9H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. customThe crude material was taken on without further purification

Sources & evidence

ORD record
ord-d5a73a013cf14a6590c636489dae1ede
Source dataset
uspto-grants-2015_08
Patent number
US09096586B2

Reaction notes

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