Water → HCID 57971710, compound

HRID 548269Notes

Reaction equation

HRID 548269 reaction equation
[CH:1]1([O:6][C:7](=[O:26])[CH2:8][NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:13][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:34]([O:36][CH2:37][CH:38]1[C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[C:44]2[C:39]1=[CH:40][CH:41]=[CH:42][CH:43]=2)=[O:35].O>C(Cl)Cl.O1CCOCC1>[CH:1]1([O:6][C:7](=[O:26])[CH2:8][N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])=[CH:15][CH:16]=2)[C:34]([O:36][CH2:37][CH:38]2[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:44]=3[C:45]3[C:50]2=[CH:49][CH:48]=[CH:47][CH:46]=3)=[O:35])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 57971657HCID 57971657, compound

Product 1

HCID 57971710HCID 57971710, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of [4-(tert-Butoxycarbonylamino-methyl)-benzylamino]-acetic acid cyclopentyl ester (0.2 g, 0.55 mmol) and 1 M Na2CO3 (1.1 mL, 1.1 mmol) in DCM (2 mL), was added slowly with stirring and ice bath cooling, a solution of 9-Fluorenylmethyl chloroformate (0.14 g, 0.55 mmol) in dioxane (1.4 mL). The mixture was stirred in the ice bath for 4 h and at room temperature overnight. The mixture was poured into water (90 mL) and extracted with diethyl ether. The organic extracts were combined, dried (MgSO4) and evaporated to dryness to afford the desired product (0.32 g, 100%). m/z 607 [M++Na]+

Workup

  1. temperatureice bath cooling
  2. extractionextracted with diethyl ether
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-a16f25580be94dc3b3219db64cc929f2
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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