Methanol → (S)-tert-Butyl 5-[(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

HRID 507035Notes

Reaction equation

HRID 507035 reaction equation
N(C(OC(C)C)=O)=N[C:3](OC(C)C)=O.[F:15][C:16]([F:58])([F:57])[C:17]1[CH:18]=[C:19]([CH:50]=[C:51]([C:53]([F:56])([F:55])[F:54])[CH:52]=1)[CH2:20][N:21]([C:45]1[N:46]=[N:47][NH:48][N:49]=1)[C@H:22]1[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:24]2[CH:36]=[C:37]([C:41]([F:44])([F:43])[F:42])[C:38]([CH3:40])=[CH:39][C:23]1=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>C1(C)C=CC=CC=1>[F:54][C:53]([F:56])([F:55])[C:51]1[CH:50]=[C:19]([CH:18]=[C:17]([C:16]([F:57])([F:15])[F:58])[CH:52]=1)[CH2:20][N:21]([C:45]1[N:46]=[N:47][N:48]([CH3:3])[N:49]=1)[C@H:22]1[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])[C:24]2[CH:36]=[C:37]([C:41]([F:42])([F:43])[F:44])[C:38]([CH3:40])=[CH:39][C:23]1=2

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59432487(S)-tert-Butyl 5-[(3,5-bistrifluoromethylbenzyl)-(2H-tetrazol-5-yl)amino)-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

Product 1

HCID 11585492(S)-tert-Butyl 5-[(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add diisopropyl azodicarboxylate (0.56 mL, 3.94 mmol) to a solution of (S)-tert-butyl 5-[(3,5-bistrifluoromethylbenzyl)-(2H-tetrazol-5-yl)amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (2.10 g, 3.29 mmol) and triphenylphosphine (1.03 g, 3.94 mmol) in methanol (0.20 mL, 4.94 mmol) and toluene (30 mL) at 0° C. under nitrogen. Warm the mixture to room temperature and stir for 12 h. Add silica gel, remove the solvents under reduced pressure and purify the residue by column chromatography on silica gel, eluting with ethyl acetate/hexanes (1:3), to provide the title compound as a colorless oil (2.04 g, 95%). APCI MS m/z 653 (M+H)+.

Workup

  1. customAdd silica gel, remove the solvents under reduced pressure
  2. custompurify the residue by column chromatography on silica gel
  3. washeluting with ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-e1d5ec225d5f4d6a8600315609b92a60
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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