Triphenylphosphine → HCID 59432484, compound

HRID 507101Notes

Reaction equation

HRID 507101 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:21]2[C:13](=[CH:14][C:15]3[CH2:16][O:17][CH2:18][C:19]=3[CH:20]=2)[C@@H:12]([N:22]([CH2:28][C:29]2[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=2)[C:23]2[N:24]=[N:25][NH:26][N:27]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:43]([O:47][CH2:48][CH2:49]O)([CH3:46])([CH3:45])[CH3:44].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[C:21]2[C:13](=[CH:14][C:15]3[CH2:16][O:17][CH2:18][C:19]=3[CH:20]=2)[C@@H:12]([N:22]([CH2:28][C:29]2[CH:30]=[C:31]([C:39]([F:40])([F:41])[F:42])[CH:32]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:34]=2)[C:23]2[N:24]=[N:25][N:26]([CH2:49][CH2:48][O:47][C:43]([CH3:46])([CH3:45])[CH3:44])[N:27]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 242322-(Tert-butoxy)ethan-1-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 59432391HCID 59432391, compound

Product 1

HCID 59432484HCID 59432484, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-9-[(3,5-bis-trifluoromethyl-benzyl)-(2H-tetrazol-5-yl)-amino]-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester (Example 73, Step 6) (0.167 mmol) in dichloromethane (20 mL), add 2-tert-butoxy-ethanol (0.835 mmol) and triphenylphosphine (0.501 mmol). To this solution, add diethyl azodicarboxylate (0.501 mmol) dropwise at room temperature. After stirring for 12 h, remove the solvent under vacuum. Chromatograph the intermediate over silica gel, eluting with ethyl acetate/hexane (2-35%) to afford the title compound as an oil. MS (ES+): 699 (M+H).

Workup

  1. customremove the solvent under vacuum
  2. washChromatograph the intermediate over silica gel, eluting with ethyl acetate/hexane (2-35%)

Sources & evidence

ORD record
ord-14ddd317df8c4b64965a9f7f7e674dc7
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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