(2S)-2-Amino-3,3-dimethyl-1-butanol → (1aR,5aR)-2-(4-Methanesulfonyl-pyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid ((S)-1-Hydroxymethyl-2,2-dimethyl-propyl)-amide

HRID 1623957Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([N:11]2[C:18]3[C@@H:17]4[CH2:19][C@@H:16]4[CH2:15][C:14]=3[C:13]([C:20](O)=[O:21])=[N:12]2)[CH:6]=1)(=[O:4])=[O:3].[NH2:23][C@@H:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:25][OH:26]>>[OH:26][CH2:25][C@@H:24]([NH:23][C:20]([C:13]1[C:14]2[CH2:15][C@H:16]3[CH2:19][C@H:17]3[C:18]=2[N:11]([C:7]2[CH:6]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:10]=[CH:9][N:8]=2)[N:12]=1)=[O:21])[C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

Reactant 2

HCID 2734079(2S)-2-Amino-3,3-dimethyl-1-butanol

HCID 68182389(1aR,5aR)-2-(4-(methylsulfonyl)pyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid

Product 1

HCID 86669695(1aR,5aR)-2-(4-Methanesulfonyl-pyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid ((S)-1-Hydroxymethyl-2,2-dimethyl-propyl)-amide

Procedure

The title compound was prepared in a manner similar to that described in Method G, using (1aR,5aR)-2-(4-(methylsulfonyl)pyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid and (S)-2-amino-3,3-dimethylbutan-1-ol. LCMS m/z=419.6 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.44-0.48 (m, 1H), 1.05 (s, 9H), 1.23-1.28 (m, 1H), 2.21 (t, J=5.8 Hz, 1H), 2.26-2.32 (m, 1H), 2.79-2.85 (m, 1H), 2.94 (d, J=16.8 Hz, 1H), 3.04 (dd, J=16.6 and 6.3 Hz, 1H), 3.16 (s, 3H), 3.67-3.74 (m, 1H), 3.94-4.04 (m, 2H), 6.96 (d, J=9.2 Hz, 1H), 7.69 (dd, J=5.0 and 1.5 Hz, 1H), 8.38 (s, 1H), 8.72 (d, J=5.0 Hz, 1H).

Sources & evidence

ORD record: ord-3ae6daee13bb400fbcce723710c25130
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778950B2

Reaction notes

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