Hydrochloric Acid → HCID 2876384, compound

HRID 1472993Notes

Reaction equation

HRID 1472993 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](N[C@H](C(O)=O)C)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-:16].[Na+].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].Cl.[OH2:30]>C1(C)C=CC=CC=1>[CH2:22]([O:21][C:19]([NH:1][CH:4]([CH2:9][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[C:5]([OH:30])=[O:16])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 29891421HCID 29891421, compound

Product 1

HCID 2876384HCID 2876384, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
2.5 °C

Procedure

To a mixture of 4-nitro phenyl alanine (500 g), sodium hydroxide (162 g) and water (5000 ml) maintained at 0 to 5° C., was added drop wise 50% benzyl chloroformate in toluene (977 g). The reaction mixture was allowed to slowly come to room temperature and further stirred overnight. The reaction mixture was cooled to 10° C. and the pH was adjusted to 2 with dilute HCl. The residue precipitated was filtered and dried to yield pure 2-Benzyloxycarbonylamino-3-(4-nitro-phenyl)-propionic acid (600 g) as an off white powder with a melting point of 123-127° C. The product was characterized by IH NMR (CDCl3+DMSOd6) δ 3-3.20 (m, 2H, CH2), 4.30 (m, 1H, CH), 4.90 (s, 2H, CH2), 7.20 (m, 6H, Ar & NH), 7.40 (d, 2H, Ar), 8.05 (d, 2H, Ar)

Workup

  1. temperatureThe reaction mixture was cooled to 10° C.
  2. customThe residue precipitated
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-2913e67a897b4f8d8e346f46915e18eb
Source dataset
uspto-grants-2015_04
Patent number
US09012677B2

Reaction notes

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