Triethylamine → HCID 86751659, compound

HRID 2294734Notes

Reaction equation

HRID 2294734 reaction equation
[CH:1]1([CH2:7][C@H:8]2[C@H:12]([C@@H:13]([OH:19])[CH2:14][NH:15][CH:16]3[CH2:18][CH2:17]3)[O:11][C:10]([CH3:21])([CH3:20])[N:9]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:36]([O:43][C:44](ON1C(=O)CCC1=O)=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:36]([O:43][C:44]([N:15]([CH2:14][C@@H:13]([C@@H:12]1[O:11][C:10]([CH3:21])([CH3:20])[N:9]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:8]1[CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[OH:19])[CH:16]1[CH2:17][CH2:18]1)=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 516892Sodium BicarbonateHCID 86751658HCID 86751658, compound

Product 1

HCID 86751659HCID 86751659, compoundYield 123.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 180 mg (0.45 mmol) of tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(S)-2-(cyclopropylamino)-1-hydroxyethyl]-2,2-dimethyl-3-oxazolidinecarboxylate, 0.126 ml (0.98 mmol) of triethylamine and 136 mg (0.545 mmol) of N-(benzyloxycarbonyloxy)succinimide in 5 ml of methylene chloride is stirred at room temperature for 2 hours. Subsequently, the residue is poured on to ice and 2N sodium bicarbonate solution and then extracted three times with 150 ml of ether each time. The organic phase is washed with 70 ml of water, then dried over magnesium sulphate and evaporated. There are obtained 296 mg of tert-butyl (4S,5R)-5-[(S)-2-[1-(benzyloxy)-N-cyclopropylformamido]-1-hydroxyethyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate as a colourless oil; MS: 531 (M+H)+.

Workup

  1. extractionextracted three times with 150 ml of ether each time
  2. washThe organic phase is washed with 70 ml of water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-cb2ce9e65ea14ce899683560bef32d06
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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