Methanol → HCID 131729367, compound

HRID 420278Notes

Reaction equation

HRID 420278 reaction equation
[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:7]([CH2:11][C@H:12]2[C@H:20]3[C@@H:16]([N:17]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=4)C(=O)[O:19]3)[CH2:15][S:14](=[O:34])(=[O:33])[CH2:13]2)=[CH:6][C:3]=1[CH:4]=O.[CH2:35]([NH2:37])[CH3:36].CO.[BH3-]C#N.[Na+].C([O-])([O-])=O.[K+].[K+].C(Cl)[Cl:51].CO>CC(O)=O>[ClH:51].[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:7]([CH2:11][C@H:12]2[C@H:20]([OH:19])[C@@H:16]([NH:17][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=3)[CH2:15][S:14](=[O:34])(=[O:33])[CH2:13]2)=[CH:6][C:3]=1[CH2:4][NH:37][CH2:35][CH3:36]

Participants

8

Reactant 6

HCID 887MethanolHCID 6341EthylamineHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 21226129Dichloromethane methanolHCID 131729366HCID 131729366, compound

Product 1

HCID 131729367HCID 131729367, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-amino-5-[(3aR*,7S*,7aS*)-3-(3-tert-butyl-benzyl)-2,5,5-trioxo-octahydro-1-oxa-5lambda*6*-thia-3-aza-inden-7-ylmethyl]-3-fluoro-benzaldehyde (0.12 g, 0.245 mmol) in CH2Cl2-MeOH 2:1 (3 mL) was added a 2M solution of ethylamine in MeOH (0.18 mL, 0.397 mmol). After stirring for 3 h at 25° C. the pH was adjusted to 4 with AcOH and the imine was reduced with NaBH3CN (0.027 g 85%, 0.367 mmol). After 20 min the reaction mixture was basified with saturated K2CO3 solution and extracted with EtOAc. Combined organic layers were washed with water and brine, dried over MgSO4, filtered and evaporated. The title compound was obtained after flash-chromatography on silica gel (CH2Cl2 to CH2Cl2-MeOH 20:1) as a beige solid: TLC (CH2Cl2-MeOH 19:1) Rf=0.39; ESIMS [M+H]+=517.

Workup

  1. extractionextracted with EtOAc
  2. washCombined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-96cb638a81174fbb9946294d1d3c777f
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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