3-Ethyl-4-hydroxy-5-methyl-benzoic acid tert-butyl ester → 3-Ethyl-4-[(S)-2-hydroxy-3-(2-hydroxy-acetylamino)-propoxy]-5-methyl-benzoic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([OH:14])=[C:9]([CH2:15][CH3:16])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=C(C(=N)NO)C=C(C)C=1O[CH2:23][C@@H:24]([OH:31])[CH2:25][NH:26][C:27](=[O:30])[CH2:28][OH:29])C>>[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][CH2:23][C@@H:24]([OH:31])[CH2:25][NH:26][C:27](=[O:30])[CH2:28][OH:29])=[C:9]([CH2:15][CH3:16])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]Participants
3
Procedure
3-ethyl-4-[(S)-2-hydroxy-3-(2-hydroxy-acetylamino)-propoxy]-5-methyl-benzoic acid tert-butyl ester (5.94 g) is prepared starting from the above 3-ethyl-4-hydroxy-5-methyl-benzoic acid tert-butyl ester (6.53 g, 27.6 mmol) following the procedures given for N—((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide. LC-MS: tR=0.87 min; [M+H]+=368.11; 1H NMR (CDCl3): δ1.17 (t, J=7.5 Hz, 3H), 1.53 (s, 9H), 2.28 (s, 3H), 2.66 (q, J=7.5 Hz, 2H), 3.17-3.26 (m, 1H), 3.38-3.46 (m, 1H), 3.65-3.75 (m, 2H), 3.83 (d, J=5.5 Hz, 2H), 3.91-3.97 (m, 1H), 5.28 (d, J=5.3 Hz, 1H), 5.54 (t, J=5.5 Hz, 1H), 7.59 (s, 1H), 7.60 (s, 1H), 7.68 (t, J=5.5 Hz, 1H).
Sources & evidence
- ORD record
- ord-3a21234f4b6e4e5d95f4490c1fecdb77
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410151B2
Reaction notes
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