tert-Butanol → [1-[3-(3-Pyridinyl)propyl]-4-(3-pyridinyl)butyl]carbamic acid 1,1-dimethylethyl ester
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH:10]([CH2:14][CH2:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)C(O)=O)[CH:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.C([N:42]([CH2:45]C)CC)C.[C:47]([OH:51])([CH3:50])([CH3:49])[CH3:48]>>[CH3:48][C:47]([O:51][C:45](=[O:30])[NH:42][CH:10]([CH2:9][CH2:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)([CH3:50])[CH3:49]Participants
5
Procedure
As in Example 36, 8.8 g of alpha-[3-(3-pyridinyl)propyl]-3-pyridinepentanoic acid, when reacted with 9.1 g of diphenylphosphorylazide in 75 mL of t-butanol containing 4.1 mL of triethylamine furnished 11.1 g of product. Purification of the crude by HPLC (ethyl acetate-methanol; 13:1) yielded 5.5 g of 1-[3-(3-pyridinyl)propyl]-4-(3-pyridinyl)butyl]carbamic acid 1,1-dimethylethyl ester as an oil.
Sources & evidence
- ORD record
- ord-911d36d904bd45fab6147fe551994962
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04788206
Reaction notes
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