1-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid → HCID 86702125, compound

HRID 873609Notes

Reaction equation

HRID 873609 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5](OC2CCN(C(OC(C)(C)C)=O)CC2)=[CH:4][CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:28]2[CH2:31][CH:30]([C:32]([NH:34][C:35]3[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][CH:36]=3)=[O:33])[CH2:29]2)[N:23]=1.C(OC(N1CC(C(O)=O)C1)=O)C1C=CC=CC=1>>[C:2]1([NH:1][C:39]([C:38]2[CH:37]=[CH:36][C:35]([NH:34][C:32]([CH:30]3[CH2:29][N:28]([C:24]4[N:23]=[N:22][CH:27]=[CH:26][CH:25]=4)[CH2:31]3)=[O:33])=[CH:43][CH:42]=2)=[O:40])[CH:21]=[CH:20][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 109882141-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acidHCID 22181157tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylateHCID 86702126HCID 86702126, compound

Product 1

HCID 86702125HCID 86702125, compound

Procedure

The title compound was prepared as described in Example 1A, substituting aniline for tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate and 4-(1-(pyridazin-3-yl)azetidine-3-carboxamido)benzoic acid for 1-(benzyloxycarbonyl)azetidine-3-carboxylic acid. 1 H NMR (400 MHz, DMSO-d6/D2O) δ ppm 8.53 (dd, J=4.4, 1.3 Hz, 1H), 7.98-7.92 (m, 2H), 7.77-7.65 (m, 5 H), 7.38-7.24 (m, 3 H), 7.15-7.07 (m, 1H), 4.49 (t, J=9.0 Hz, 2H), 4.46-4.38 (m, 2H), 4.00-3.81 (m, 1H); MS (ESI(+)) m/e 374 (M+H)+.

Sources & evidence

ORD record
ord-4a8865e12178469580fee8dc7945ce88
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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