(S)-3-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester → 4-{2-[5-Acetylamino-2-(1-tert-butoxycarbonylmethyl-2,2-diethoxy-ethylsulfamoyl)-phenoxy]-ethyl}-naphthalene-1-carboxylic acid methyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:38])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][C:21]=1OCC1C=CC=CC=1)(=[O:19])=[O:18])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[CH3:39][O:40][C:41]([C:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]([CH2:53][CH2:54][OH:55])=[CH:45][CH:44]=1)=[O:42]>>[CH3:39][O:40][C:41]([C:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]([CH2:53][CH2:54][O:55][C:21]2[CH:22]=[C:23]([NH:26][C:27](=[O:29])[CH3:28])[CH:24]=[CH:25][C:20]=2[S:17](=[O:19])(=[O:18])[NH:16][CH:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:38])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[CH:45][CH:44]=1)=[O:42]Participants
3
Reactant 2
Product 1
Procedure
Synthesized by the Mitsunobu reaction between (S)-3-(4-Acetylamino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester from step 8 of Route J and 4-(2-hydroxyethyl)-naphthlene-1-carboxylic acid methyl ester from above. 1H NMR (400 MHz, CD3OD) 8.96(d, 1H), 8.16(dd, 2H), 7.71(d, 2H), 7.61(m, 2H), 7.55(d, 1H), 6.69(d, 1H), 5.57(d, 1H), 4.42(t, 2H), 4.21(d, 1H), 3.98(s, 3H), 3.72(t, 2H) 3.62(m, 1H), 3.42(m, 2H), 3.40(m, 1H), 3.14(m, 1H), 2.37(d, 2H), 2.16(s, 3H), 1.37(s, 9H), 1.00(t, 3H), 0.90(t, 3H).
Sources & evidence
- ORD record
- ord-0aaaad766d254a0da8e516104ca3678c
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06875765B2
Reaction notes
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