2,3-Dihydro-1,4-benzodioxin-5-carboxylic acid → (1S,3S,5S)-3-{[(2,3-dihydro-benzo[1,4]dioxine-5-carbonyl)-amino]-methyl}-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

HRID 2064795Notes

Reaction equation

HRID 2064795 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:21]2[CH:22]=[CH:23][CH:24]=[C:25]([C:26](O)=[O:27])[C:20]=2[O:19][CH2:18][CH2:17]1>>[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][NH:15][C:26]([C:25]2[C:20]3[O:19][CH2:18][CH2:17][O:16][C:21]=3[CH:22]=[CH:23][CH:24]=2)=[O:27])[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 781842,3-Dihydro-1,4-benzodioxin-5-carboxylic acidHCID 58278675(1S,3S,5S)-tert-Butyl 3-(aminomethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Product 1

HCID 67081183(1S,3S,5S)-3-{[(2,3-dihydro-benzo[1,4]dioxine-5-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 2,3-dihydro-benzo[1,4]dioxine-5-carboxylic acid. LC-MS (acidic): tR=0.97 min; [M+H]+=375.1. 1H-NMR (CDCl3): δ=0.61 (bs, 1H); 0.76-0.82 (m, 1H); 1.47-1.52 (m, 1H); 1.51 (s, 9H); 1.89 (bd, J=13.2 Hz, 1H); 2.42-2.47 (m, 1H); 3.34-3.74 (m, 3H); 4.30-4.35 (m, 1H); 4.32 (bs, 2H); 4.44 (bs, 2H); 6.91-7.05 (m, 2H); 7.67-7.73 (m, 1H); 8.43 (bs, NH).

Sources & evidence

ORD record
ord-558b747fe2754de9b7d99e13aee86312
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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