1-Benzofuran-4-carboxylic acid → (1S,3S,5S)-3-{[(benzofuran-4-carbonyl)-amino]-methyl}-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

HRID 2064793Notes

Reaction equation

HRID 2064793 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][NH2:15])[CH2:12][C@H:11]2[C@@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:16]1[C:20]2=[CH:21][CH:22]=[CH:23][C:24]([C:25](O)=[O:26])=[C:19]2[CH:18]=[CH:17]1>>[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][NH:15][C:25]([C:24]2[CH:23]=[CH:22][CH:21]=[C:20]3[O:16][CH:17]=[CH:18][C:19]=23)=[O:26])[CH2:12][C@H:11]2[C@@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 223241171-Benzofuran-4-carboxylic acidHCID 58278675(1S,3S,5S)-tert-Butyl 3-(aminomethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Product 1

HCID 67081514(1S,3S,5S)-3-{[(benzofuran-4-carbonyl)-amino]-methyl}-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Procedure

prepared by reaction of (1S,3S,5S)-3-aminomethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester with benzofuran-4-carboxylic acid (M. A. Eissenstat et al. J. Med. Chem. 1995, 38, 3094-3105). LC-MS (acidic): tR=1.00 min; [M+H]+=357.1. 1H-NMR (CDCl3): δ=0.58 (bs, 1H); 0.80-0.86 (m, 1H); 1.52 (s, 9H); 1.52-1.59 (m, 1H); 1.79 (bd, J=13.3 Hz, 1H); 2.51-2.60 (m, 1H); 3.24-3.30 (m, 1H); 3.60-3.64 (m, 2H); 4.45-4.52 (m, 1H); 7.32 (t, J=7.9 Hz, 1H); 7.47 (bs, 1H); 7.61 (d, J=8.2 Hz, 1H); 7.65 (d, J=7.5 Hz, 1H); 7.70 (bs, 1H); 8.43 (bs, 1H).

Sources & evidence

ORD record
ord-c166e627c5f34d2bb0a5016c39621cea
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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