Sodium Hydroxide → 5-[(3S*,4S*,5R*)-5-(3-tert-Butyl-benzylamino)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-ylmethyl]-2-nitro-benzoic acid

HRID 420298Notes

Reaction equation

HRID 420298 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH:9]=[C:8]([CH2:10][C@H:11]2[C@H:16]([OH:17])[C@@H:15]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:21]=3)[CH2:14][S:13](=[O:31])(=[O:30])[CH2:12]2)[CH:7]=[CH:6][C:5]=1[N+:32]([O-:34])=[O:33].BrCC1C=CC([N+]([O-])=O)=C(C=1)C(OC)=O.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[C:26]([C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][NH:18][C@H:15]1[CH2:14][S:13](=[O:31])(=[O:30])[CH2:12][C@@H:11]([CH2:10][C:8]2[CH:7]=[CH:6][C:5]([N+:32]([O-:34])=[O:33])=[C:4]([CH:9]=2)[C:3]([OH:35])=[O:2])[C@@H:16]1[OH:17])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 13399988Methyl 5-(bromomethyl)-2-nitrobenzoateHCID 1317293775-[(3S*,4S*,5R*)-5-(3-tert-butyl-benzylamino)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-ylmethyl]-2-nitro-benzoic acid methyl ester

Product 1

HCID 1317293765-[(3S*,4S*,5R*)-5-(3-tert-Butyl-benzylamino)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-ylmethyl]-2-nitro-benzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-[(3S*,4S*,5R*)-5-(3-tert-butyl-benzylamino)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-ylmethyl]-2-nitro-benzoic acid methyl ester (434 mg, 0.86 mmol; prepared from methyl 5-(bromomethyl)-2-nitrobenzoate using a procedure analogous to that used in example 1) and NaOH (30% in H2O, 1 mL, 7.4 mmol) in anhydrous THF (5 mL) was stirred at 80° C. for 1 h. The reaction mixture was diluted with EtOAc and quenched with 2N aq. HCl to pH 2. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated to yield the product as a yellow gum: ESIMS [M+H]+=491, LCMS RtI=0.97 min.

Workup

  1. customquenched with 2N aq. HCl to pH 2
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-404e07c89fc04f6aac2ae12cf5e136df
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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