Triethylamine → HCID 86747660, compound

HRID 375746Notes

Reaction equation

HRID 375746 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]([NH:38][CH3:39])[CH2:6][S:7][CH2:8][C:9]1[C:27]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])=[CH:26][C:25]([O:36][CH3:37])=[CH:24][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:12])=[O:4].[C:40]([O:59][CH2:60][CH2:61][C:62](Cl)=[O:63])([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(N(CC)CC)C>C(Cl)Cl>[Si:29]([O:28][C:27]1[C:9]([CH2:8][S:7][CH2:6][C@H:5]([N:38]([C:62](=[O:63])[CH2:61][CH2:60][O:59][C:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH3:39])[C:3]([O:2][CH3:1])=[O:4])=[C:10]([CH:24]=[C:25]([O:36][CH3:37])[CH:26]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:12])([C:32]([CH3:34])([CH3:35])[CH3:33])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18992056HCID 18992056, compoundHCID 54329215HCID 54329215, compound

Product 1

HCID 86747660HCID 86747660, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.64 g of p-nitrobenzyl (R)-2-[[[2-(methoxycarbonyl)-2-(methylamino)-ethyl]thio]methyl]-3-(tert-butyldimethylsilyloxy)-5-methoxybenzoate and 0.58 g of 3-trityloxypropionyl chloride in 6 ml of methylene chloride was treated at 0° C. with 0.17 g of triethylamine. The mixture was stirred at 0° C. for 30 minutes, then diluted with methylene chloride, and washed successively with 5% sodium bicarbonate solution and brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated in vacuo. The residual oil was chromatographed on silica gel using ethyl acetate/hexane (1:2, v/v) as eluent to yield 0.65 g of p-nitrobenzyl (R)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2-[[[2-(3-trityloxypropionyl-methylamino)-2-methoxycarbonyl-ethyl]thio]methyl]-benzoate as an oil.

Workup

  1. washwashed successively with 5% sodium bicarbonate solution and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-dcce8e0c29a749c8a4424f863a279876
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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