Triethylamine → HCID 22355046, compound

HRID 891038Notes

Reaction equation

HRID 891038 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH2:12]([O:19][C:20]([O:22]N1C(=O)CCC1=O)=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([N:32](CC)CC)C>C(Cl)Cl>[C:20]([C:8]([NH2:32])([C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[C:9]([OH:11])=[O:10])([O:19][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 145334-Aminophenylacetic acidHCID 83172Benzyl succinimido carbonate

Product 1

HCID 22355046HCID 22355046, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-amino phenylacetic acid (9 g, 60 mmol) and N-(benzyloxycarbonyloxy)succinimide (15 g, 60 mmol) in CH2Cl2 was added enough triethylamine to form a homogeneous solution. The mixture was stirred at room temperature for 30 min and then CH2Cl2 was removed by rotavapor. The resulting residue was dissolved in water and acidified with 5% HCl. The solid thus formed was filtered and washed with 5% HCl, water, and diethyl ether to give 12 g (70%) of Cbz-aminophenylacetic acid as a brownish powder. 1H-NMR (300 MHz, DMSO-d6): 3.48 (s, 2H), 5.13 (s, 2H), 7.14 (d, 2H), 7.29–7.45 (m, 7H), 9.73 (s, 1H).

Workup

  1. customto form a homogeneous solution
  2. customCH2Cl2 was removed by rotavapor
  3. dissolutionThe resulting residue was dissolved in water
  4. customThe solid thus formed
  5. filtrationwas filtered
  6. washwashed with 5% HCl, water, and diethyl ether

Sources & evidence

ORD record
ord-55044219a8c942ec9a5504c00a1e475c
Source dataset
uspto-grants-2006_02
Patent number
US07001921B1

Reaction notes

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