Acetic Acid → HCID 178487815, compound

HRID 1422933Notes

Reaction equation

HRID 1422933 reaction equation
C(O)(=O)C.[CH2:5]([O:12][C:13](=[O:38])[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]2(O)[NH:34][C:33]3[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([O:35][CH3:36])[N:31]=4)[N:26]=[CH:25][C:24]=3[O:23][CH2:22]2)[CH2:17][CH2:16]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([BH3-])#N.[Na+]>ClCCl.CO>[CH2:5]([O:12][C:13](=[O:38])[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([CH:21]2[NH:34][C:33]3[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([O:35][CH3:36])[N:31]=4)[N:26]=[CH:25][C:24]=3[O:23][CH2:22]2)[CH2:17][CH2:16]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 178487816HCID 178487816, compound

Product 1

HCID 178487815HCID 178487815, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

Acetic acid (10 μL, 0.17 mmol, 5.4 eq) is added at room temperature to a stirred solution of [trans-4-(3-hydroxy-6-methoxy-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-carbamic acid benzyl ester (15 mg, 0.03 mmol, 1.0 eq) in dichloromethane (3 mL) and methanol (3 mL), followed by sodium cyanoborohydride (10 mg, 0.16 mmol, 5.0 eq). After 30 minutes stirring at room temperature, the reaction mixture is extracted with ethyl acetate (3×10 mL) and a saturated ammonium chloride aqueous solution (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 10:1, v/v) to afford [trans-4-(6-methoxy-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-carbamic acid benzyl ester as a white solid (11 mg, 76% yield).

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a residue that
  6. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-a3438146542c4445b36a2937750e3e61
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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