Triethylamine → HCID 86746114, compound

HRID 1885427Notes

Reaction equation

HRID 1885427 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]([CH3:63])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][Si:51]([CH:58]([CH3:60])[CH3:59])([CH:55]([CH3:57])[CH3:56])[CH:52]([CH3:54])[CH3:53])[CH:46]([O:61][CH3:62])[CH2:45]2)[CH:7]([CH3:64])[CH:6](O)[CH2:5][C:4]1=[O:66])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[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]([CH3:63])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][Si:51]([CH:55]([CH3:57])[CH3:56])([CH:52]([CH3:54])[CH3:53])[CH:58]([CH3:60])[CH3:59])[CH:46]([O:61][CH3:62])[CH2:45]2)[CH:7]([CH3:64])[CH:6]=[CH:5][C:4]1=[O:66])[CH3:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86746113HCID 86746113, compound

Product 1

HCID 86746114HCID 86746114, compoundYield 58.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-triisopropylsilyloxy-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 (150 mg, 0.16 mmol) in MeCl2 (5.0 ml) containing triethylamine (92.2 mg, 0.91 mmol) and 4-dimethylaminopyridine (61 mg, 0.49 mmol) at 0° C., was treated with methanesulfonyl chloride (69.6 mg, 0.61 mmol). After stirring at RT for 2.5 hr, the reaction mixture was diluted with MeCl2 (10 ml) and water. The aqueous layer was separated and extracted with additional MeCl2. After drying over magnesium sulfate, the solvent was removed in vacuo. The residue was chromatographed over SiO2 (10 g). Elution with n-hexane/ethyl acetate (3:1) yielded 17-ethyl-1-hydroxy-12-[2'-(4"-triisopropylsilyloxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos- 14,18-diene-2,3,10,16-tetraone (86.6 mg, 58%). Mass Spec: C52H89NO11Si (930.36) FAB+Li:1090 (M+ +Li+MATRIX) 936 (M+Li).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with additional MeCl2
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe residue was chromatographed over SiO2 (10 g)
  6. washElution with n-hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-d66f9a6fc5534a0482997499ac1aee14
Source dataset
uspto-grants-1992_09
Patent number
US05143918

Reaction notes

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