Triphenylphosphine → (3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propoxy}-benzyl)-carbamic acid tert-butyl ester

HRID 902662Notes

Reaction equation

HRID 902662 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:36][C:37]1[C:69]([C:70]([F:73])([F:72])[F:71])=[CH:68][CH:67]=[CH:66][C:38]=1[CH2:39][N:40]([CH2:52][CH:53]([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH2:41][CH2:42][CH2:43]OC1C=C(N)C=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:43][CH2:42][CH2:41][N:40]([CH2:39][C:38]2[CH:66]=[CH:67][CH:68]=[C:69]([C:70]([F:71])([F:72])[F:73])[C:37]=2[Cl:36])[CH2:52][CH:53]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 101287483-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethylamino]-propoxy}-phenylamineHCID 18369568tert-butyl N-((3-hydroxyphenyl)methyl)carbamate

Product 1

HCID 69252950(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propoxy}-benzyl)-carbamic acid tert-butyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3-Hydroxy-benzyl)-carbamic acid tert butyl ester was dissolved in THF, triphenylphosphine (0.44 g, 2.2 mmole), 3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethylamino]-propoxy}-phenylamine (1.0 g, 2.3 mmole) and DIAD (0.43 ml, 2.2 mmole) were added subsequently. The mixture was stirred overnight at room temperature. The reaction was concentrated, chromatographed on silica gel (0 to 15% EtOAc/hexanes) to give the titled compound (0.51 g, 48%). MH+652.0

Workup

  1. concentrationThe reaction was concentrated
  2. customchromatographed on silica gel (0 to 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-536c3c198da645608ab335dc77576999
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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