Carbon tetrabromide → HCID 56615139, compound

HRID 375754Notes

Reaction equation

HRID 375754 reaction equation
[C:1]([Si:5]([CH3:45])([CH3:44])[O:6][C:7]1[CH:8]=[C:9]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[C:10]2[CH2:21][S:20][CH2:19][C@@H:18]([CH2:22]O)[NH:17][C:16](=[O:24])[C@@H:15]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:14][O:13][C:12](=[O:33])[C:11]=2[C:34]=1[CH3:35])([CH3:4])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:47].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:47][CH2:22][C@@H:18]1[NH:17][C:16](=[O:24])[C@@H:15]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])[CH2:14][O:13][C:12](=[O:33])[C:11]2[C:34]([CH3:35])=[C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:45])[CH3:44])[CH:8]=[C:9]([O:36][Si:37]([C:40]([CH3:42])([CH3:43])[CH3:41])([CH3:38])[CH3:39])[C:10]=2[CH2:21][S:20][CH2:19]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 54462572HCID 54462572, compound

Product 1

HCID 56615139HCID 56615139, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 103 mg of tert-butyl (4R, 7S)-12, 14-bis (tertbutyldimethylsilyloxy)-1,3,4,5,6,7,8, 10-octahydro-4-hydroxymethyl-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate in 2 ml of methylene chloride was treated with 99 mg of carbontetrabromide and 79 mg of triphenylphosphine, and then stirred at 20° C. for 15 minutes. The solution was chromatographed on silica gel using ethyl acetate/hexane (1:3, v/v) as eluent to yield tert-butyl (4R, 7S)-4-bromomethyl-12,14-bis-(tert-butyldimethylsilyloxy)-1,3,4,5,6,7,8,10-octahydro-11-methyl-6,10-dioxo-9,2,5-benzooxathiaazacyclododecine-7-carbamate. This material was treated with ammonium fluoride in methanol in an analogous manner to the procedure described in Example 13 to yield, after crystallization from ethyl acetate/hexane, tert-butyl (4R, 7S)-4-bromomethyl- 1,3,4,5,6,7,8,10-octahydro-12,14-dihydroxy-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate as a white solid.

Workup

  1. customThe solution was chromatographed on silica gel

Sources & evidence

ORD record
ord-b30a8942e540462aa65cc09c7445922e
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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