Water → HCID 66987908, compound

HRID 333416Notes

Reaction equation

HRID 333416 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].O.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:19].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C@H:2]([NH:1][C:18]([O:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[O:19])[C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 10856719O-Methyl-L-tyrosine methyl ester

Product 1

HCID 66987908HCID 66987908, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g (4.8 mmol) of methyl(S)-2-amino-3-(4-methoxyphenyl)propionate (cf. preparation 2-1) is diluted in 30 mL of dichloromethane. The solution is cooled in a bath of cold water, and 1.4 g (7.2 mmol) of 4-nitrophenyl chloroformate and 1.2 mL (7.2 mmol) of diisopropylethylamine are then added. After warming to room temperature, the reaction medium is stirred for 2 hours. The solution is poured into water and then extracted with dichloromethane. The organic phase is dried and then evaporated. The crude product obtained is used in the following step without further purification.

Workup

  1. additionare then added
  2. extractionextracted with dichloromethane
  3. customThe organic phase is dried
  4. customevaporated

Sources & evidence

ORD record
ord-9f75dd7f3bcd41df80f6a154aeb2408b
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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