alpha-Chlorohydrin, (+)- → HCID 49871975, compound

HRID 245104Notes

Reaction equation

HRID 245104 reaction equation
[CH:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[C:14]([O:16][CH3:17])[N:15]=2)[C:10]([OH:12])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18]([C:20]1[CH:21]=[C:22]([CH:27]=[C:28]([CH3:31])[C:29]=1[OH:30])[C:23]([NH:25]O)=[NH:24])[CH3:19].Cl[CH2:33][C@@H:34]([OH:37])[CH2:35][OH:36]>>[CH:1]1([C:7]2[CH:8]=[C:9]([C:10]3[O:12][N:25]=[C:23]([C:22]4[CH:27]=[C:28]([CH3:31])[C:29]([O:30][CH2:33][C@@H:34]([OH:37])[CH2:35][OH:36])=[C:20]([CH2:18][CH3:19])[CH:21]=4)[N:24]=3)[CH:13]=[C:14]([O:16][CH3:17])[N:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 148904alpha-Chlorohydrin, (+)-HCID 67491148HCID 67491148, compoundHCID 178436626HCID 178436626, compound

Product 1

HCID 49871975HCID 49871975, compound

Procedure

The title compound is prepared in analogy to Example 3 starting from 2-cyclohexyl-6-methoxy-isonicotinic acid, 3-ethyl-4,N-dihydroxy-5-methyl-benzamidine and (S)-3-chloro-1,2-propanediol; LC-MS: tR=1.16 min, [M+H]+=468.08; 1H NMR (CDCl3): δ1.33 (t, J=7.5 Hz, 3H), 1.34-1.40 (m, 1H), 1.40-1.52 (m, 2H), 1.57-1.69 (m, 2H), 1.77-1.84 (m, 1H), 1.87-1.95 (m, 2H), 1.99-2.08 (m, 2H), 2.41 (s, 3H), 2.70-2.81 (m, 3H), 3.83-4.00 (m, 4H), 4.03 (s, 3H), 4.15-4.21 (m, 1H), 7.32 (s, 1H), 7.49 (s, 1H), 7.88 (s, 1H), 7.90 (s, 1H).

Sources & evidence

ORD record
ord-27f7287444a64f669032cf8ec952ff93
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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