Triethylamine → N-BOC-m-Benzoyl-L-Phenylalanine

HRID 34686Notes

Reaction equation

HRID 34686 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=1)[CH2:12][C@@H:13]([C:15]([OH:17])=[O:16])[NH2:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][C:29]([O:32][C:33](ON=C(C1C=CC=CC=1)C#N)=[O:34])([CH3:31])[CH3:30]>O.CC(C)=O>[C:33]([NH:14][C@H:13]([C:15]([OH:17])=[O:16])[CH2:12][C:11]1[CH:18]=[CH:19][CH:20]=[C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)([O:32][C:29]([CH3:31])([CH3:30])[CH3:28])=[O:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 14233367m-benzoyl-L-phenylalanine

Product 1

HCID 14233370N-BOC-m-Benzoyl-L-Phenylalanine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A suspension of 2.175 g of m-benzoyl-L-phenylalanine in 25 ml of water and 1.15 g of triethylamine was treated with 3.35 g of BOC-ON in 40 ml of acetone. After 3 h, acetone was removed and the aqueous residue was extracted three times with ether (discarded). The aqueous solution was acidified to pH 2 with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried (MgSO4) and stripped. The residue was triturated for 7 days with petroleum ether. The waxy insoluble solid was triturated for 14 days with an additional portion of petroleum ether and finally for 7 days with a third portion. The resulting white solid weighed 1.786 g after vacuum drying, [α]D25 +22.2±0.9°, C=0.86 g/100 ml ethanol. Anal.: Calcd. for C21H23NO5 :C, 68.28; H, 6.28; N, 3.79. Found: C, 68.01; H, 6.49; N, 3.68.

Workup

  1. customacetone was removed
  2. extractionthe aqueous residue was extracted three times with ether (discarded)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried (MgSO4)
  5. customThe residue was triturated for 7 days with petroleum ether
  6. customThe waxy insoluble solid was triturated for 14 days with an additional portion of petroleum ether and finally for 7 days with a third portion
  7. customdrying

Sources & evidence

ORD record
ord-0315a666c64b43fd98a8efb3ebeb32e5
Source dataset
uspto-grants-1988_08
Patent number
US04762881

Reaction notes

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