Sodium Carbonate → HCID 20577182, compound

HRID 1266243Notes

Reaction equation

HRID 1266243 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:14]=2)[CH:10]=[CH:11][CH:12]=1)=[O:5].C(=O)([O-])[O-].[Na+].[Na+].O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[Cl:55][C:56]1[CH:57]=[C:58]([CH:64]=[CH:65][CH:66]=1)[C@@H:59]([OH:63])[C:60](O)=[O:61]>C(OCC)(=O)C>[Cl:55][C:56]1[CH:57]=[C:58]([C@H:59]([OH:63])[C:60]([NH:2][CH2:3][C:4]([NH:6][C:7]2[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:14]=3)[CH:10]=[CH:11][CH:12]=2)=[O:5])=[O:61])[CH:64]=[CH:65][CH:66]=1

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 10868DicyclohexylcarbodiimideHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 69712085Methyl 3'-[(aminoacetyl)amino][1,1'-biphenyl]-3-carboxylate hydrochloride

Product 1

HCID 20577182HCID 20577182, compoundYield 426.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
10 °C

Procedure

A suspension of methyl 3′-[(aminoacetyl)amino][1,1′-biphenyl]-3-carboxylate hydrochloride (50 g) in ethyl acetate (350 ml) is treated with 1 M aqueous sodium carbonate (250 ml) at room temperature. The lower aqueous phase is discarded, 1-hydroxybenzotriazole hydrate (10 g) and then dicyclohexylcarbodiimide (30.6 g) is added to the organic phase and the mixture is cooled to approximately 10° C. This mixture is treated with a solution of (R)-3-chloromandelic acid (5.8 g) in ethyl acetate (40 ml) over approximately 1 hour. The mixture is stirred for several hours and filtered. The filtrate is washed with 6% w/w aqueous sodium bicarbonate and water, and the organic phase is concentrated to low volume. Isopropanol is added and the organic solution is further concentrated to low volume. The organic solution is warmed to 70° C., treated with water, cooled to room temperature and the mixture is filtered to give the title product (60 g).

Workup

  1. filtrationfiltered
  2. washThe filtrate is washed with 6% w/w aqueous sodium bicarbonate and water
  3. concentrationthe organic phase is concentrated to low volume
  4. additionIsopropanol is added
  5. concentrationthe organic solution is further concentrated to low volume
  6. temperatureThe organic solution is warmed to 70° C.
  7. additiontreated with water
  8. temperaturecooled to room temperature
  9. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-b40b4e4c778644bb8dd9ed100cf4d927
Source dataset
uspto-grants-2003_04
Patent number
US06548523B2

Reaction notes

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