2-Amino-1-butanol, (+)- → (S)-N-(1-hydroxybutan-2-yl)-2-(3'-(methoxymethyl)biphenyl-4-yl)-2-methylpropanamide

HRID 1175616Notes

Reaction equation

HRID 1175616 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([CH3:21])([CH3:20])[C:17](O)=[O:18])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1.[NH2:22][C@@H:23]([CH2:26][CH3:27])[CH2:24][OH:25]>>[OH:25][CH2:24][C@@H:23]([NH:22][C:17](=[O:18])[C:16]([C:13]1[CH:12]=[CH:11][C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][O:2][CH3:1])[CH:5]=2)=[CH:15][CH:14]=1)([CH3:21])[CH3:20])[CH2:26][CH3:27]

Participants

3

Reactant 2

HCID 1200842-Amino-1-butanol, (+)-HCID 687743992-(3'-(Methoxymethyl)biphenyl-4-yl)-2-methylpropanoic acid

Product 1

HCID 16005271(S)-N-(1-hydroxybutan-2-yl)-2-(3'-(methoxymethyl)biphenyl-4-yl)-2-methylpropanamideYield 52%

Procedure

Prepared in a similar manner to Example 27 from 2-(3′-(methoxymethyl)biphenyl-4-yl)-2-methylpropanoic acid (example 39a) and (S)-2-aminobutan-1-ol. Yield: 52%. 1H NMR (DMSO-d6, 400 MHz) δ 7.61 (m, 4H), 7.44 (m, 3H), 7.31 (d, 1H, J=7.2 Hz), 6.83 (d, 1H, J=8.5 Hz), 4.57 (t, 1H, J=5.8 Hz), 4.84 (s, 2H), 3.68 (m, 1H), 3.34 (m, 1H), 3.33 (s, 3H), 3.22 (m, 1H), 1.56 (m, 1H), 1.49 (s, 6H), 1.29 (m, 1H), 0.76 (t, 3H, J=7.3 Hz). 13C NMR (DMSO-d6, 100 MHz) δ 175.5, 145.8, 139.8, 139.2, 137.8, 128.9, 126.5, 126.5, 126.4, 125.6, 125.6, 73.6, 63.0, 57.6, 52.5, 46.1, 27.1, 27.0, 23.5, 10.6. M+H=356, m.p.=73-75° C.

Sources & evidence

ORD record
ord-970017c32c1a46a89a36af10ff812fad
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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