2-Methylbenzoic acid → HCID 12967658, compound

HRID 375721Notes

Reaction equation

HRID 375721 reaction equation
CC1C=CC=CC=1C(O)=O.C(OCC)(=O)C.CCCCCC.[Si]([O:30][C:31]1[CH:32]=[C:33]([O:62][Si](C(C)(C)C)(C)C)[C:34]2[CH2:45][S:44][CH2:43][C@@H:42]([C:46]([O:48][CH3:49])=[O:47])[NH:41][C:40](=[O:50])[C@@H:39]([NH:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:38][O:37][C:36](=[O:59])[C:35]=2[C:60]=1[CH3:61])(C(C)(C)C)(C)C.[F-].[NH4+]>CO>[OH:30][C:31]1[CH:32]=[C:33]([OH:62])[C:34]2[CH2:45][S:44][CH2:43][C@@H:42]([C:46]([O:48][CH3:49])=[O:47])[NH:41][C:40](=[O:50])[C@@H:39]([NH:51][C:52]([O:54][C:55]([CH3:56])([CH3:57])[CH3:58])=[O:53])[CH2:38][O:37][C:36](=[O:59])[C:35]=2[C:60]=1[CH3:61]

Participants

6

Reactant 4

HCID 83732-Methylbenzoic acidHCID 25516Ammonium fluorideHCID 10996150HCID 10996150, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 12967658HCID 12967658, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,5-Bis (tert-butyldimethylsilyloxy)-6-[[[(R)-2-[(S)-1-tertbutoxyformamido)-3-hydroxypropionylamino]-2-methoxycarbonylethyl]thio]methyl]-2-methylbenzoic acid was lactonized in analogous manner to the procedure described in Example 1 to afford, upon chromatographic purification on silica gel using ethyl acetate/hexane (1: 3, v/v) as eluent, tert-butyl (4R, 7S)-12,14-bis (tert-butyldimethylsilyloxy)-1,3,4,5,6,7,8,10-octahydro-4-methoxycarbonyl-11-methyl-6, 10-dioxo-9, 2,5-benzooxathiaazacyclododecine-7-carbamate as a pale yellow foam. To a solution of 21.4 g of this material in 300 ml of methanol were added 3.3 g of ammonium fluoride, and the mixture was stirred for 30 minutes at room temperature. The solvent was evaporated in vacuo. The residue chromatographed on silica gel using ethyl acetate/hexane (1:1, v/v) as eluent, and the purified product was crystallized from ethyl acetate/hexane to afford 11.0 g of tert-butyl (4R,7S)-1,3,4,5,6,7,8,10-octahydro-12,14-dihydroxy-4-methoxycarbonyl-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate.

Workup

  1. customto afford, upon chromatographic purification on silica gel
  2. customThe solvent was evaporated in vacuo
  3. customThe residue chromatographed on silica gel
  4. customv/v) as eluent, and the purified product was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2a8656a942f04d7dbf32d8514dfa0790
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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