Triphenylphosphine → HCID 89832301, compound

HRID 1619026Notes

Reaction equation

HRID 1619026 reaction equation
[CH2:1]([N:4]1[CH2:8][CH:7]([CH2:9]O)[C:6]([NH:16][C:17]([NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[S:18])([C:11]2[S:15][CH:14]=[N:13][CH:12]=2)[CH2:5]1)[CH:2]=[CH2:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[CH2:1]([N:4]1[CH2:8][CH:7]2[C:6]([C:11]3[S:15][CH:14]=[N:13][CH:12]=3)([N:16]=[C:17]([NH:19][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:18][CH2:9]2)[CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 89823264HCID 89823264, compound

Product 1

HCID 89832301HCID 89832301, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-[[1-allyl-4-(hydroxymethyl)-3-thiazol-5-yl-pyrrolidin-3-yl]carbamothioyl]benzamide (60 mg, 150 μmoles) in tetrahydrofuran (1 mL) at 0° C. is added triphenylphosphine (80 mg, 30 μmoles) and di-t-butyl azodicarboxylate (88 mg, 30 μmoles). The mixture is stirred for 30 minutes at 0° C., warmed to room temperature and stirred for 1 hour. The mixture is concentrated and purified over silica gel eluting with methanol/dichloromethane (0-5%) to give the title product (26 mg, 70 p moles, 45%). ES/MS (m/e): 385 (M+H).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 1 hour
  3. concentrationThe mixture is concentrated
  4. custompurified over silica gel eluting with methanol/dichloromethane (0-5%)

Sources & evidence

ORD record
ord-64dbd295fc7a469b9643b8c99cd894e4
Source dataset
uspto-grants-2014_07
Patent number
US08772282B2

Reaction notes

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