Tris(hydroxymethyl)aminomethane → (2S,3R,4R,5S,6R)-2-(3-(4-(4-((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)butyl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol

HRID 1499299

Reaction equation

HRID 1499299 reaction equation
OCC(N[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:35]=[CH:34][C:14]([CH2:15][C:16]2[CH:17]=[C:18]([C@H:23]3[C@H:28]([OH:29])[C@@H:27]([OH:30])[C@H:26]([OH:31])[C@@H:25]([S:32][CH3:33])[O:24]3)[CH:19]=[CH:20][C:21]=2[CH3:22])=[CH:13][CH:12]=1)(C)C.[NH2:36][C:37]([CH2:42][OH:43])([CH2:40][OH:41])[CH2:38][OH:39]>>[OH:39][CH2:38][C:37]([NH:36][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][C:16]2[CH:17]=[C:18]([C@H:23]3[C@H:28]([OH:29])[C@@H:27]([OH:30])[C@H:26]([OH:31])[C@@H:25]([S:32][CH3:33])[O:24]3)[CH:19]=[CH:20][C:21]=2[CH3:22])=[CH:34][CH:35]=1)([CH2:42][OH:43])[CH2:40][OH:41]

Participants

3

Reactant 2

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 90177781(2S,3R,4R,5S,6R)-2-(3-(4-(4-((1-hydroxy-2-methylpropan-2-yl)amino)butyl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol

Product 1

HCID 90183233(2S,3R,4R,5S,6R)-2-(3-(4-(4-((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)butyl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol

Procedure

The same procedure was employed as for amine 24, using 2-amino-2-(hydroxyl-methyl)propane-1,3-diol, to provide the product 25 as the bisformate salt. 1H NMR (400 MHz, MeOH-d4) δ ppm 8.53 (s, 2 H), 6.98-7.23 (m, 7 H), 4.39 (d, J=9.3 Hz, 1 H), 4.13 (d, J=9.1 Hz, 1H), 3.94-4.03 (m, 2 H), 3.69 (s, 6 H), 3.34-3.50 (m, 3 H), 3.03-3.13 (m, 2 H), 2.58-2.69 (m, 2 H), 2.20 (s, 3 H), 2.12-2.18 (m, 3 H), 1.70 (m, 4 H). [M+H]+=537.

Sources & evidence

ORD record
ord-518bc0160ddc4762958ae4e81593a26d
Source dataset
uspto-grants-2015_12
Patent number
US09200025B2

Linked notes

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