Sodium Carbonate → HCID 53670313, compound

HRID 393445Notes

Reaction equation

HRID 393445 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[C:10]([NH:12][C:13]1[CH:24]=[CH:23][C:16]([CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[NH2:19])=[CH:15][CH:14]=1)=[O:11].[CH:25]1[C:37]2[CH:36]([CH2:38][O:39][C:40](ON3C(=O)CCC3=O)=[O:41])[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]=2[CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[C:10]([NH:12][C:13]1[CH:24]=[CH:23][C:16]([CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[NH:19][C:40]([O:39][CH2:38][CH:36]2[C:35]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:29]3[C:37]2=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:41])=[CH:15][CH:14]=1)=[O:11]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 69360872HCID 69360872, compound

Product 1

HCID 53670313HCID 53670313, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine hydrochloride salt (30 mmol, 10.59 g), N-(9-fluorenylmethoxycarbonyloxy)succinimide (30 mmol, 10.12 g) and sodium carbonate (300 mmol, 31.8 g) were added dioxane (75 mL) and water (25 mL) at room temperature. The suspension was stirred for 15 h at room temperature at which time TLC analysis of the mixture indicated the absence of starting material. The inorganic solids were filtered through celite and washed with ethyl acetate. While washing with ethyl acetate some organic compound was precipitated out from filtrate which was collected and air dried. The filtrate was concentrated under vacuum and the residue was combined with the above organic solid compound and the product was taken up in hot THF and precipatated with ether to obtain 14.1 g (81%), as a white solid, mp 230-234° C. LR MS (C31H24C12N2O5): Obs mass, 597. Calcd mass, 597, (M+Na).

Workup

  1. filtrationThe inorganic solids were filtered through celite
  2. washwashed with ethyl acetate
  3. washWhile washing with ethyl acetate some organic compound
  4. customwas precipitated out from filtrate which
  5. customwas collected
  6. customair dried
  7. concentrationThe filtrate was concentrated under vacuum
  8. customto obtain 14.1 g (81%)

Sources & evidence

ORD record
ord-0458bfcb9b4947258490d2fd20bda5a1
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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