HCID 53900326, compound → HCID 54054556, compound

HRID 234230Notes

Reaction equation

HRID 234230 reaction equation
OC1C2C[S:17]C[C@@H](C(N)=O)NC(=O)CCCCOC(=O)C=2C(C)=C(OC)C=1.[CH3:28][Si:29]([CH3:63])([C:57]([CH3:62])([CH3:61])[CH:58]([CH3:60])[CH3:59])[O:30][C:31]1[C:48]2[CH2:47][S:46][CH2:45][C@@H:44]([C:49]([NH2:51])=O)[NH:43][C:42](=[O:52])[CH2:41][CH2:40][CH2:39][CH2:38][O:37][C:36](=[O:53])[C:35]=2[C:34]([CH3:54])=[C:33]([O:55][CH3:56])[CH:32]=1>C1(C)C=CC=CC=1>[CH3:63][Si:29]([CH3:28])([C:57]([CH3:61])([CH3:62])[CH:58]([CH3:60])[CH3:59])[O:30][C:31]1[C:48]2[CH2:47][S:46][CH2:45][C@H:44]([C:49](=[S:17])[NH2:51])[NH:43][C:42](=[O:52])[CH2:41][CH2:40][CH2:39][CH2:38][O:37][C:36](=[O:53])[C:35]=2[C:34]([CH3:54])=[C:33]([O:55][CH3:56])[CH:32]=1

Participants

4

Reactant 2

HCID 53900326HCID 53900326, compoundHCID 54563454HCID 54563454, compound

Product 1

HCID 54054556HCID 54054556, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The product of Example 68 was subjected in an analogous manner to the procedure described in Example 1(f) and the resulting (R)-16-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-14-methoxy-13-methyl-6,12-dioxo-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecine-4-carboxylic acid amide was reacted in toluene with an equimolar mount of 2,4-bis-(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiaphosphetane at 60° C. for 30 min. The solvent was evaporated in vacuo, and the residue was chromatographed on silica gel using ethyl acetate/hexane (1:2, v/v) as eluent, to yield-(R)-16-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-14-methoxy-13-methyl-6,12-dioxo-1,3,4,5,6,7,8,9,1 0, 12-decahydro-11,2,5-benzoxathiaazacyclotetradecine-4-thiocarboxylic acid amide as a white foam.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-d64cf869275d46cab4c4b0eadf100516
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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