Ammonium Chloride → HCID 57563021, compound
Reaction equation
[CH3:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][CH2:12][C@H:13]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]([CH2:38][C:39]3[CH:43]=[CH:42][S:41][CH:40]=3)[C:22]3[CH:37]=[CH:36][C:25]([O:26][C:27]4[CH:35]=[CH:34][C:30]([C:31]([OH:33])=O)=[CH:29][CH:28]=4)=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)[CH3:14])=[O:9])=[C:6]([CH3:44])[N:5]=[CH:4][N:3]=1.[Cl-].[NH4+:46]>>[C:31]([C:30]1[CH:29]=[CH:28][C:27]([O:26][C:25]2[CH:36]=[CH:37][C:22]([N:21]([CH2:38][C:39]3[CH:43]=[CH:42][S:41][CH:40]=3)[CH:18]3[CH2:19][CH2:20][N:15]([C@H:13]([CH3:14])[CH2:12][CH2:11][NH:10][C:8]([C:7]4[C:2]([CH3:1])=[N:3][CH:4]=[N:5][C:6]=4[CH3:44])=[O:9])[CH2:16][CH2:17]3)=[CH:23][CH:24]=2)=[CH:35][CH:34]=1)(=[O:33])[NH2:46]Participants
Procedure
Using general procedure E, COMPOUND 302 (103 mg, 0.17 mmol) and ammonium chloride (23 mg, 0.42 mmol) afforded COMPOUND 303 as a white solid (160 mg, 100%). 1H NMR (CDCl3) δ 0.87-1.21 (m, 2H), 1.01 (d, 3H, J=6.0 Hz), 1.49-1.60 (m, 1H), 1.71-1.85 (m, 3H), 2.11-2.22 (m, 1H), 2.53 (s, 6H), 2.55-2.62 (m, 1H), 2.71-2.92 (m, 3H), 3.25-3.38 (m, 1H), 3.48-3.61 (m, 1H), 3.82-3.94 (m, 1H), 3.83 (s, 2H), 5.77 (br s, 2H), 6.62 (d, 1H, J=8.1 Hz), 6.87 (d, 2H, J=8.4 Hz), 6.92 (d, 2H, J=8.4 Hz), 7.04 (d, 1H, J=3.3 Hz), 7.26-7.32 (m, 1H), 7.73 (d, 2H, J=7.8 Hz), 8.81 (br s, 1H), 8.89 (s, 1H). 13C NMR (CDCl3) δ 13.80, 22.33, 29.50, 30.86, 31.03, 40.62, 43.96, 46.17, 52.59, 56.51, 60.90, 114.86, 116.77, 121.09, 121.80, 126.32, 126.87, 129.62, 131.31, 141.91, 146.46, 158.01, 162.73, 163.46, 166.72, 169.17. ES-MS m/z 613 (M+H). Anal. Calcd. for C34H40N6O3S.0.3CH2Cl2: C, 64.55; H, 6.41; N, 13.17. Found: C, 64.29; H, 6.38; N, 12.96.
Sources & evidence
- ORD record
- ord-dad02694fc6a45e28e0b1cf5c76a7f65
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491735B2
Reaction notes
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