Dichloromethane → HCID 20737862, compound

HRID 354271Notes

Reaction equation

HRID 354271 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1)=[O:7])([CH3:4])(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O.C(Cl)(OCC1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44]2[C:39]1=[CH:40][CH:41]=[CH:42][CH:43]=2)=O>CCOCC>[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:22][CH:23]=1)([O:5][CH2:1][CH:4]1[C:43]2[C:44](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:45]2[C:50]1=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:7]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 343679-Fluorenylmethyl chloroformateHCID 69332259HCID 69332259, compound

Product 1

HCID 20737862HCID 20737862, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the above (S)-4-(1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxybenzoic acid was added CH2Cl2 (10 mL) and TFA (10 mL). The mixture was stirred at room temp for 1 hr Et2O was added to the mixture and resulting solid was collected. The solid was dissolved in water (100 mL), dioxane (50 mL) and NaHCO3 (4.4 g). Fmoc-Cl (3.34 g, 12.9 mmol) was added to the solution, and the resulting mixture was stirred for 20 hr at room temp. The mixture was washed with Et2O (×2) and aqueous layer was separated. The layer was acidified by the addition of 1 N HCl. The mixture was extracted with EtOAc. The extract was washed with water, brine, dried over MgSO4 and evaporated in vacuo to afford 5.36 g (91%) (S)-4-(1-Fmoc-2-pyrrolidinyl)methoxybenzoic acid as a viscous oil, which was crystallized on standing.

Workup

  1. additionwas added to the mixture
  2. customresulting solid
  3. customwas collected
  4. dissolutionThe solid was dissolved in water (100 mL)
  5. washThe mixture was washed with Et2O (×2) and aqueous layer
  6. customwas separated
  7. additionThe layer was acidified by the addition of 1 N HCl
  8. extractionThe mixture was extracted with EtOAc
  9. washThe extract was washed with water, brine
  10. dry with materialdried over MgSO4
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-a4e517fd80e64206b12915c996ed5959
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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