Diisopropylethylamine → (S)-tert-butyl 4-(3-(5-(2-(tert-butoxycarbonylamino)pent-4-ynamido)pent-1-ynyl)phenoxy)piperidine-1-carboxylate
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:8]=[C:9]([CH:24]=[CH:25][CH:26]=1)[O:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.[CH3:27][C:28]([O:31][C:32]([NH:34][C@H:35]([C:39](O)=[O:40])[CH2:36][C:37]#[CH:38])=[O:33])([CH3:30])[CH3:29].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:28]([O:31][C:32]([NH:34][C@@H:35]([CH2:36][C:37]#[CH:38])[C:39]([NH:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:8]=[C:9]([CH:24]=[CH:25][CH:26]=1)[O:10][CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:15][CH2:16]1)=[O:40])=[O:33])([CH3:30])([CH3:29])[CH3:27]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring solution of tert-butyl 4-(3-(5-aminopent-1-ynyl)phenoxy)piperidine-1-carboxylate (0.59 g, 1.6 mmol), Boc-L-propargylglycine (0.35 g, 1.6 mmol), N-ethyldiisopropylamine (0.73 ml, 4.1 mmol) in DMF (20 ml) was added HBTU (0.81 g, 2.1 mmol). The resulting solution was stirred at room temperature overnight. (S)-tert-Butyl 4-(3-(5-(2-(tert-butoxycarbonylamino)pent-4-ynamido)pent-1-ynyl)phenoxy)piperidine-1-carboxylate was isolated and purified over Gilson HPLC as a colorless oil. MH+ 554.44
Sources & evidence
- ORD record
- ord-9ea3572cf47b4c958729d9ffd3e3464d
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633322B2
Reaction notes
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