Triethylamine → HCID 86585782, compound

HRID 2299645Notes

Reaction equation

HRID 2299645 reaction equation
[OH:1][CH2:2][C:3]1[CH:39]=[CH:38][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([N:12]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:13][C@H:14]([O:23][Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26])[CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][C:5]=2[CH:4]=1.C(N(CC)CC)C.[CH3:47][S:48](Cl)(=[O:50])=[O:49]>ClCCl>[O:16]([CH2:15][C@@H:14]([O:23][Si:24]([CH2:27][CH3:28])([CH2:25][CH3:26])[CH2:29][CH3:30])[CH2:13][N:12]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH:10]1[CH2:9][CH2:8][CH2:7][C:6]2[CH:38]=[CH:39][C:3]([CH2:2][O:1][S:48]([CH3:47])(=[O:50])=[O:49])=[CH:4][C:5]=2[CH2:11]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 56983775HCID 56983775, compound

Product 1

HCID 86585782HCID 86585782, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-(3-hydroxymethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-[(2S)-3-phenoxy-2-(triethylsilyl-oxy)propyl]-tert-butoxycarbonylamine (1.93 g) and triethylamine (0.58 ml) in dichloromethane (40 ml) was added dropwise methanesulfonyl chloride (0.27 ml) under ice-cooling. After stirring at room temperature for 6 hours, the reaction mixture was washed successively with water, sodium bicarbonate solution, water and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo to afford crude N-[(2S)-3-phenoxy-2-(triethylsilyloxy)propyl]-N-(3-methylsulfonyloxymethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]-tert-butoxycarbonylamine (2.18 g) which was used without purification.

Workup

  1. temperaturecooling
  2. washthe reaction mixture was washed successively with water, sodium bicarbonate solution, water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5a6eb46857324ac4bb1205ccdd8dc599
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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