Water → Fmoc-phenylalanine

HRID 1087874

Reaction equation

HRID 1087874 reaction equation
N[C@H:2]([C:10](O)=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([N:15]([CH2:18][CH3:19])CC)C.[C:20](=[O:23])([O-])[O-:21].[OH2:24].O1[CH2:30][CH2:29][O:28][CH2:27]C1>>[CH:2]1[C:10]2[CH:30]([CH2:29][O:28][C:27]([NH:15][C@H:18]([C:20]([OH:21])=[O:23])[CH2:19][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[O:24])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]=2[CH:2]=[CH:10][CH:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6140L-PhenylalanineHCID 8471TriethylamineHCID 19660Carbonate IonHCID 312751,4-Dioxane2×

Product 1

HCID 978331Fmoc-phenylalanineYield 75%

Conditions

Temperature
0 °C

Procedure

0.83 g of L-phenylalanine (5 mmoles) are dissolved in aqueous dioxan (1: 2, 12 ml) containing 1.4 ml of triethylamine (10 mmoles). The mixture is cooled to 0° C. and 2.05 g (5 mmoles of the preceding carbonate dissolved in 4 ml of dioxan added at one time. After two hours at 0° C., 20 ml of water are added, followed by extraction twice with 20 ml of ether. The aqueous phase is then acidified (pH 2-3) with 6 N HCl followed by extraction three times with 50 ml of ethyl acetate. This is followed by drying over MgSO4 and evaporation. The product obtained crystallizes from ethyl acetate and petroleum-ether, and 1.44 g of the desired derivative obtained (yield 75%).

Workup

  1. additionadded at one time
  2. extractionfollowed by extraction twice with 20 ml of ether
  3. extractionfollowed by extraction three times with 50 ml of ethyl acetate
  4. dry with materialby drying over MgSO4 and evaporation
  5. customThe product obtained
  6. customcrystallizes from ethyl acetate and petroleum-ether, and 1.44 g of the desired derivative
  7. customobtained (yield 75%)

Sources & evidence

ORD record
ord-ed3c8d975fb94393be521c0025c9887f
Source dataset
uspto-grants-1990_10
Patent number
US04960881

Linked notes

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