Methanol → t-butyl N-[N-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-N-[(7-cyano-2-naphthyl)methyl]sulfamoyl]-N-methylcarbamate

HRID 362529Notes

Reaction equation

HRID 362529 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:33][C:34]3[CH:43]=[CH:42][C:41]4[C:36](=[CH:37][C:38]([C:44]#[N:45])=[CH:39][CH:40]=4)[CH:35]=3)[S:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:24])=[O:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:46]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:33][C:34]3[CH:43]=[CH:42][C:41]4[C:36](=[CH:37][C:38]([C:44]#[N:45])=[CH:39][CH:40]=4)[CH:35]=3)[S:22]([N:25]([CH3:46])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:24])=[O:23])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15392237HCID 15392237, compound

Product 1

HCID 15392239t-butyl N-[N-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-N-[(7-cyano-2-naphthyl)methyl]sulfamoyl]-N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

t-Butyl N-[N-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-N-[(7-cyano-2-naphthyl)methyl]sulfamoyl]carbamate obtained in Reference Example 42 (172 mg) was dissolved in 0.7 ml of tetrahydrofuran, 139 mg of triphenylphosphine, 32 μl of methanol and 83 μl of diethyl azodicarboxylate was added to the solution at 0° C., and then the mixture was stirred at room temperature for 40 minutes. The reaction solution was evaporated, and the resulting residue was purified by silica gel column chromatography using hexane:ethyl acetate (85:15) as the eluent to give 153 mg of t-butyl N-[N-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-N-[(7-cyano-2-naphthyl)methyl]sulfamoyl]-N-methylcarbamate.

Workup

  1. customThe reaction solution was evaporated
  2. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4bb76539494c448ebba73dc111cf800f
Source dataset
uspto-grants-1999_02
Patent number
US05869501

Reaction notes

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