Triphenylphosphine → HCID 59432459, compound

HRID 507122Notes

Reaction equation

HRID 507122 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].O[CH2:44][CH2:45][N:46]1[C:50](=[O:51])[C:49]2=[CH:52][CH:53]=[CH:54][CH:55]=[C:48]2[C:47]1=[O:56].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=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]([CH2:44][CH2:45][N:46]3[C:47](=[O:56])[C:48]4[C:49](=[CH:52][CH:53]=[CH:54][CH:55]=4)[C:50]3=[O:51])[N:27]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 77499N-(2-Hydroxyethyl)phthalimideHCID 5462977Diethyl azodicarboxylateHCID 59432391HCID 59432391, compound

Product 1

HCID 59432459HCID 59432459, 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 72, Step 6) (0.84 mmol) and N-(2-Hydroxyethyl)phthalimide (2.51 mmol) in dichloromethane (10 mL), add triphenylphosphine (2.51 mmol) followed by dropwise addition of diethylazodicarboxylate (2.51 mmol). After stirring at room temperature for 14 h, remove the solvent under vacuum. Chromatograph over silica gel eluting with ethyl acetate/hexane (5-50%) to provide the title compound as a colorless foam. MS (ES+): 772 (M+H).

Workup

  1. customremove the solvent under vacuum

Sources & evidence

ORD record
ord-af0e9f4b2cbd46dc95796a08dcd5a743
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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