Triethylamine → N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

HRID 1736620Notes

Reaction equation

HRID 1736620 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:16][C:17]([O:20][C:21](ON=C(C1C=CC=CC=1)C#N)=[O:22])([CH3:19])[CH3:18].CCN(CC)CC>O.O1CCOCC1.CCOCC>[C:21]([NH:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1)([O:20][C:17]([CH3:19])([CH3:18])[CH3:16])=[O:22]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 137064-Nitro-3-phenyl-L-alanineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Product 1

HCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanineYield 90.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred suspension of 50.45 g (240 mmole) of 4-nitro-L-phenylalanine in 140 ml water was added a solution of 65.11 g (264.4 mmole; 1.1 eq) of BOC-ON in 140 ml dioxane and 53 ml (380.3 mmole; 1.58 eq) of Et3N. The gradually cleared solution was stirred at room temperature for 4 hours. The reaction mixture was poured into 410 ml water and extracted with ether (5×330 ml). The aqueous layer was acidified to pH 1.15 with 6N HCl and then extracted with EtOAc (5×330 ml). The EtOAc extracts were pooled and dried over with MgSO4, filtered and evaporated under reduced pressure to give a crude residue. This residue was dissolved in 300 ml ether, the solvent was removed under reduced pressure to give 67.61 g (90.8%) product (1) as a pale yellow foam. 1HNMR (CDCl3, δ)=8.17 & 7.38 (d & d, 4H), 5.15 & 4.55 (m & m, 2H), 3.20 (m, 2H), 1.38 (2s, 9H).

Workup

  1. extractionextracted with ether (5×330 ml)
  2. extractionextracted with EtOAc (5×330 ml)
  3. dry with materialdried over with MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give a crude residue
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bac6dd383f964883acde92d297cd0fc4
Source dataset
uspto-grants-1996_07
Patent number
US05541287

Reaction notes

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