Hydrochloric Acid → (4S,7S,10aS)-4-(tert-butoxycarbonylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid

HRID 529480Notes

Reaction equation

HRID 529480 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH2:14][S:13][C@H:12]2[CH2:16][CH2:17][CH2:18][C@@H:19]([C:20]([O:22]C)=[O:21])[N:11]2[C:10]1=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH2:14][S:13][C@H:12]2[CH2:16][CH2:17][CH2:18][C@@H:19]([C:20]([OH:22])=[O:21])[N:11]2[C:10]1=[O:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 68292140(4S,7S,10aS)-methyl 4-(tert-butoxycarbonylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

Product 1

HCID 68292173(4S,7S,10aS)-4-(tert-butoxycarbonylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (4S,7S,10aS)-methyl 4-(tert-butoxycarbonylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (0.139 g, 0.387 mmol) in MeOH (6 mL) was added NaOH (1 N in water, 387 μL, 0.387 mmol). The mixture was stirred at rt overnight. HPLC showed only 20% conversion. Additional NaOH (1 N in water, 387 μL, 0.387 mmol) was added and the reaction was stirred for an additional 3 days. The mixture was cooled with ice-water and the reaction was carefully neutralized with aqueous 1 N HCl to pH<7. The reaction was extracted with DCM. The organic layer was washed with water, dried over MgSO4, filtered and concentrated to give (4S,7S,10aS)-4-(tert-butoxycarbonylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid (133 mg, 0.386 mmol, 99% yield) as a white solid.

Workup

  1. stirringthe reaction was stirred for an additional 3 days
  2. extractionThe reaction was extracted with DCM
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f578effcecdc457281060564cf935dd5
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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