Phosgene → 1-({4-(tert-Butyl-dimethyl-silanyloxy)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidine-2-carbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester

HRID 1445422Notes

Reaction equation

HRID 1445422 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:16][NH:15]2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].[C:27]([O-:30])(O)=O.[Na+].C(Cl)(Cl)=O.[CH2:36]([NH:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)[CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][Si:20]([C:23]([CH3:25])([CH3:24])[CH3:26])([CH3:22])[CH3:21])[CH2:16][N:15]2[C:27](=[O:30])[N:43]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])[CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 57956448Hept-6-enyl-(4-methoxy-benzyl)-amineHCID 686756681-{[4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 686758741-({4-(tert-Butyl-dimethyl-silanyloxy)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidine-2-carbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 124 (5.88 g, 15.4 mmol) was dissolved in THF (200 ml), NaHCO3 (s) (appr. 10 ml) was added followed by phosgene-solution (20% in toluene, 15.9 ml, 30.7 mmol). The reaction mixture was stirred vigorously for 1 h and then filtrated, evaporated and redissolved in DCM (200 ml). NaHCO3 (s) (appr. 10 ml) was added followed by hept-6-enyl-(4-methoxy-benzyl)-amine (5.58 g, 23.9 mmol). The reaction mixture was stirred at room temperature overnight, filtrated and evaporated on silica. The crude product was purified by column chromatography on silica (EtOAc/n-Heptane 25/75-50/50) to give the title compound (4.9 g, 50%).

Workup

  1. filtrationfiltrated
  2. customevaporated
  3. dissolutionredissolved in DCM (200 ml)
  4. additionNaHCO3 (s) (appr. 10 ml) was added
  5. stirringThe reaction mixture was stirred at room temperature overnight
  6. filtrationfiltrated
  7. customevaporated on silica
  8. customThe crude product was purified by column chromatography on silica (EtOAc/n-Heptane 25/75-50/50)

Sources & evidence

ORD record
ord-271cd91e78094bc9810efc0300140e51
Source dataset
uspto-grants-2010_02
Patent number
US07666834B2

Reaction notes

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