L-Phenylalanine → HCID 11153906, compound

HRID 2373091Notes

Reaction equation

HRID 2373091 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:19](=O)([O:28][CH2:29][CH:30]1[C:43]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[O:37][C:36]2[C:31]1=[CH:32][CH:33]=[CH:34][CH:35]=2)[O:20]N1C(=O)CCC1=O>O.O1CCOCC1>[CH:42]1[C:43]2[CH:30]([CH2:29][O:28][C:19]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[O:20])[C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:37][C:38]=2[CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 6140L-PhenylalanineHCID 10340Sodium CarbonateHCID 19902701HCID 19902701, compound

Product 1

HCID 11153906HCID 11153906, compoundYield 89.43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of 0.467 g of L-phenylalanine and 0.6 g of sodium carbonate in 6 mL of water and 6 mL of dioxane was added dropwise at 0° C. a solution of 1.0 g of succinimidyl 9-xanthenylmethyl carbonate in 10 mL of dioxane over a period of 10 minutes. The mixture was stirred at room temperature for four hours, washed with ether (2×15 mL), and the ether layer was discarded. The aqueous layer was acidified with 10% HCl (Congo Red) and extracted with EtOAc (3×15 ml). The combined organic extracts were dried over MgSO4 and the solvent was evaporated in vacuo to give 1.02 g (89.43%) of the crude Xmoc-Phe-OH as a colorless oil. Crystallization from Skelly B -EtOAc (3:1) gave 0.77 g (67.51%) of the pure Xmoc-Phe-OH as white crystals, m.p. 143°-145° C.; IR KBr: 3420 (NH and OH), 1720 (C=O)cm-1 ; 1H NMR (CDCl3): δ 2.90-3.30 (m, 2H, CH2Ar), 4.40-4.45 (m, 3H, CH--CH2O), 4.65 (m, 1H, NCH), 5.18 (b, 1H, NH), 6.85-7.60 (m, 13H, aryl); [α]23D -3.1 (c=1, EtOAc), [α]23 546 -3.4 (c=1, EtOAc).

Workup

  1. washwashed with ether (2×15 mL)
  2. extractionextracted with EtOAc (3×15 ml)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-90c3273793e74af793bb40343f2d0d69
Source dataset
uspto-grants-1992_03
Patent number
US05101059

Reaction notes

Loading…