Methanol → HCID 11657467, compound

HRID 507084Notes

Reaction equation

HRID 507084 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:6][N:7]([C:30]1[NH:34][N:33]=[N:32][N:31]=1)[CH:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[C:10]2[C:21]([CH3:29])=[C:22]([C:25]([F:28])([F:27])[F:26])[CH:23]=[CH:24][C:9]1=2.CO.[C:46]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[F:39][C:38]([F:41])([F:40])[C:36]1[CH:35]=[C:5]([CH:4]=[C:3]([C:2]([F:42])([F:1])[F:43])[CH:37]=1)[CH2:6][N:7]([C:30]1[N:31]=[N:32][N:33]([CH3:46])[N:34]=1)[CH:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH:18]([CH3:19])[CH3:20])=[O:16])[C:10]2[C:21]([CH3:29])=[C:22]([C:25]([F:26])([F:27])[F:28])[CH:23]=[CH:24][C:9]1=2

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178427867HCID 178427867, compound

Product 1

HCID 11657467HCID 11657467, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (+/−)-isopropyl 5-[(3,5-bistrifluoromethyl-benzyl)-(1H-tetrazol-5-yl)-amino]-9-methyl-8-trifluormethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (87 mg, 0.139 mmol), methanol (0.564 mL, 13.9 mmol), triphenyl phosphine (73 mg, 0.278 mmol) in dry dichloromethane (3.4 mL) at 0° C., under nitrogen, add diethyl azodicarboxylate (0.128 mL, 0.278 mmol). Stir the reaction mixture at room temperature for 3 h. Remove the solvents under reduced pressure and purify the residue by flash chromatography, eluting with hexanes/ethyl acetate to afford the title compound (47 mg, 53%). MS (ES+): 639 (M+H).

Workup

  1. customRemove the solvents under reduced pressure
  2. custompurify the residue by flash chromatography
  3. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-e45cdfff448741bfa1690679a9a7ac12
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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