Stearyl Alcohol → HCID 69686684, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH2:22][OH:23])=[N:12][C:11]=2[CH:24]([CH3:26])[CH3:25])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH:27]([C:31]([O-:33])=[O:32])[C:28]([O-:30])=O.[CH2:34](O)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51].[N-]=C=O>>[NH:27]([C:28]([O:23][CH2:22][C:13]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:24]([CH3:26])[CH3:25])[N:12]=1)=[O:30])[C:31]([O:33][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH3:34])=[O:32]Participants
Procedure
The compound 89 (245 mg, 0.6 mmol) was converted to the iminodicarboxylate with N-octadecanyloxycarbonyl isocyanate prepared from 1-octadecanol (297 mg, 1.1 mmol) and N-chloroarbonyl isocyanate (106 mg, 1 mmol) in the same manner as the example 82 to give the compound 100 (295 mg, 66%). Mp. 96-98° C. Rf 0.46 (EtOAc). 1H-NMR (CDCl3): δH0.88 (3 H, t like, CH3), 1.25-1.30 (30 H, m, --CH2 --), 1.31 (6 H, d, J 6.9 Hz, (CH3)2CH), 1.62 (2 H, m, --CH2 --), 3.18 (1 H, sep, J 6.9 Hz, (CH3)2CH), 4.14 (2 H, t, J 6.9 Hz, CH2O), 5.23 (2 H, s, NCH2), 5.31 (2 H, s, OCH2), 6.71 (2 H, d, J 1.8 Hz, arom 2- and 6-H), 6.77 (2 H, d-like, 4-pyridyl 2- and 6-H), 6.95 (1 H, bs, NH), 7.06 (1 H, t, J 1.8 Hz, arom 4-H), 8.45 (2 H, d-like, 4-pyridyl 3- and 5-H). IR(CHCl3)cm-1 : 3394 (NH), 1791 and 1764 (NCO), 1715 (NCOO). Elementary analysis (for C39H56N4O4SCl2) Calcd. : C, 62.64% H, 7.55% N, 7.49% S, 4.29% Cl, 9.48% Found: C, 62.86% H, 7.73% N, 7.43% S, 4.00% Cl, 9.07%
Sources & evidence
- ORD record
- ord-2297c2e56d5647ccb2a2dc5205822871
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06054591
Reaction notes
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