Sodium Carbonate → HCID 54022445, compound

HRID 2297316Notes

Reaction equation

HRID 2297316 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][C@H:8]([NH2:31])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[C:39](Cl)([O:41][CH2:42][CH:43]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:49]2[C:44]1=[CH:45][CH:46]=[CH:47][CH:48]=2)=[O:40]>O1CCOCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:32])[CH2:7][C@H:8]([NH:31][C:39]([O:41][CH2:42][CH:43]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:49]=2[C:50]2[C:55]1=[CH:54][CH:53]=[CH:52][CH:51]=2)=[O:40])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 54011543HCID 54011543, compound

Product 1

HCID 54022445HCID 54022445, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred suspension of (R)-3-amino-5-(4′-heptyloxybiphenyl-4-yl)pentanoic acid tert-butyl ester (crude, 3.14 g) in 50% aqueous 1,4-dioxane (40 ml) were added Na2CO3 (1.19 g, 11.2 mmol) and FmocCl (1.28 g, 4.95 mmol). After being stirred for 1 h, the mixture was diluted with sat. brine (100 ml) and extracted with CH2Cl2 (100 ml×3). The combined extracts were dried over anhydrous Na2SO4 and concentrated in vacuo to give (R)-3-(9-fluorenylmethoxycarbonylamino)-5-(4′-heptyloxybiphenyl-4-yl)pentanoic acid tert-butyl ester (crude, 3.34 g) which was used for the next step without further purification.

Workup

  1. extractionextracted with CH2Cl2 (100 ml×3)
  2. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee8e7f64eeb342cd9de6b4448a323715
Source dataset
uspto-grants-2002_12
Patent number
US06489440B1

Reaction notes

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