Pentachlorophenol → Ethyl ((benzyloxy)carbonyl)-L-phenylalanylglycinate

HRID 1580550Notes

Reaction equation

HRID 1580550 reaction equation
[C:1]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].ClC1C(O)=C(Cl)C(Cl)=C(Cl)C=1Cl.C([N+]#[C-])(C)C.Cl.[CH2:41]([O:43][C:44](=[O:47])[CH2:45][NH2:46])[CH3:42]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:41]([O:43][C:44](=[O:47])[CH2:45][NH:46][C:20](=[O:22])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH3:42]

Participants

7

Reactant 4

HCID 992PentachlorophenolHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 150783Isopropyl isocyanideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 12628842Ethyl ((benzyloxy)carbonyl)-L-phenylalanylglycinateYield 82%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 6.0 (20 mM) N-carbobenzoxy-L-phenylalanine, 5.3 g (20 mM) pentachlorophenol, and 2.0 g (30 mM) is isopropyl isonitrile in 40 ml chloroform was mixed with a solution of 2.8 g (20 mM) glycine ethyl ester hydrochloride and 2.02 g (20 mM) triethylamine in 30 ml chloroform. The mixture was heated at 50°C for 24 hours and evaporated. The residue was taken up in 150 ml ethyl acetate. The solution was washed sequentially with 100 ml water, 120 ml 1-N hydrochloric acid, four times 120 ml 5% sodium bicarbonate solution, and again with 100 ml water, then dried with desiccated sodium sulfate and evaporated. When the residue was crystallized from ethyl acetate and petroleum ether, 6.3 g N-carbobenzoxy-L-phenylalanyl-glycine ethyl ester was obtained (82 percent yield). Recrystallizing from ethyl acetate and petroleum ether reduced the yield to 5.4 g (70%). M.P. 107°-108.5°C. [ α]D25 = - 17.1° (C = 2, in ethanol).

Workup

  1. customevaporated
  2. washThe solution was washed sequentially with 100 ml water, 120 ml 1-N hydrochloric acid, four times 120 ml 5% sodium bicarbonate solution
  3. dry with materialagain with 100 ml water, then dried with desiccated sodium sulfate
  4. customevaporated
  5. customWhen the residue was crystallized from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-89945cfb45ce4ab28282d1c7ff2ed7b2
Source dataset
uspto-grants-1976_01
Patent number
US03933783

Reaction notes

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