2-Nitrobenzenesulfonyl chloride → HCID 131717516, compound

HRID 1885429Notes

Reaction equation

HRID 1885429 reaction equation
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([OH:50])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]([O:55][Si:56]([CH:63]([CH3:65])[CH3:64])([CH:60]([CH3:62])[CH3:61])[CH:57]([CH3:59])[CH3:58])[CH2:5][C:4]1=[O:66])[CH3:2].C(N(C(C)C)CC)(C)C.[N+:76]([C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][C:80]=1[S:85](Cl)(=[O:87])=[O:86])([O-:78])=[O:77]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][S:85]([C:80]3[CH:81]=[CH:82][CH:83]=[CH:84][C:79]=3[N+:76]([O-:78])=[O:77])(=[O:86])=[O:87])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]([O:55][Si:56]([CH:60]([CH3:62])[CH3:61])([CH:57]([CH3:59])[CH3:58])[CH:63]([CH3:65])[CH3:64])[CH2:5][C:4]1=[O:66])[CH3:2]

Participants

6

Reactant 3

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 56974216HCID 56974216, compound

Product 1

HCID 131717516HCID 131717516, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 17-ethyl-1-hydroxy-14-triisopropylsilyloxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]-octacos-18-ene-2,3,10,16-tetraone(1.0 g, 1.06 mmol) in MeCl2 (20 ml) containing 4-dimethylaminopyridine (312 mg, 2.55 mmol) and diisopropylethylamine (319 mg, 2.47 mmol) was treated with o-nitrobenzenesulfonyl chloride (476 mg, 2.14 mmol). After stirring at RT for 18 hr, the reaction mixture was diluted with MeCl2 (20 ml). The resultant suspension was filtered and the filtrate passed over SiO2 (90 g). Elution with n-hexane/ethyl acetate (1:1) yielded 17-ethyl-1-hydroxy-14-triisopropylsilyloxy-12-[2'-(4"-o-nitrobenzenesulfonyloxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (933 mg, 78%) and starting material (206 mg, 20%).

Workup

  1. filtrationThe resultant suspension was filtered
  2. washElution with n-hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-15265de59e964d95b8ebd31485eafba3
Source dataset
uspto-grants-1992_09
Patent number
US05143918

Reaction notes

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