Dicyclohexylcarbodiimide → HCID 53706041, compound

HRID 442003Notes

Reaction equation

HRID 442003 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:30][CH:31]([CH3:33])[CH3:32])[NH:5][C:6](=[O:29])[C@@H:7]([CH3:28])[NH:8][C:9](=[O:27])[C@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[NH2:11].FC(F)(F)C(O)=O.COC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)[C@H](CC1C=CC(OCC2C=CC=CC=2)=CC=1)N.[C:76]([O:80][C:81]([NH:83][C@H:84]([C:94](O)=[O:95])[CH2:85][O:86][CH2:87][C:88]1[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=1)=[O:82])([CH3:79])([CH3:78])[CH3:77].C1(N=C=NC2CCCCC2)CCCCC1>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:30][CH:31]([CH3:33])[CH3:32])[NH:5][C:6](=[O:29])[C@@H:7]([CH3:28])[NH:8][C:9](=[O:27])[C@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[NH:11][C:94](=[O:95])[C@H:84]([CH2:85][O:86][CH2:87][C:88]1[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=1)[NH:83][C:81]([O:80][C:76]([CH3:79])([CH3:77])[CH3:78])=[O:82]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 54570025HCID 54570025, compoundHCID 70631663O-Benzyl-L-tyrosyl-D-alanyl-L-leucine methyl ester trifluoroacetic acid salt

Product 1

HCID 53706041HCID 53706041, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Conditions

Temperature
-5 °C

Procedure

Nα -t-Butoxycarbonyl-O-benzyl-L-seryl-O-benzyl-L-tyrosyl-D-alanyl-L-leucine methyl ester is prepared from 10 mmoles of O-benzyl-L-tyrosyl-D-alanyl-L-leucine methyl ester is prepared from 10 mmoles of O-benzyl-L-tyrosyl-D-alanyl-L-leucine methyl ester trifluoroacetic acid salt by neutralizing to litmus with triethylamine in the cold and then adding 1.4 ml. (10 mmol) of additional triethylamine (pH 8.5). The cold solution is treated with 2.95 g. (10 mmol) of Nα -t-butoxycarbonyl-O-benzyl-L-serine, 1.35 g. of 1-hydroxybentriazole and 2.2 g. of dicyclohexylcarbodiimide. The mixture is stirred for two and one-half hours at -5° C. and overnight at room temperature. The mixture is filtered, the solid rinsed with dimethylformamide and the filtrate evaporated at 40° C. under reduced pressure. The residue is dissolved in 50 ml. of ethyl acetate and 200 ml. of ether and washed three times with 5% sodium bicarbonate solution and with saturated salt solution, dried over magnesium sulfate and evaporated. The residue is crystallized from a minimum of methanol by adding ether; 6.6 g. The product is recrystallized from methanol-ether; 6 g.; m.p. 67°-71° C.

Workup

  1. additionthen adding 1.4 ml
  2. additionThe cold solution is treated with 2.95 g
  3. filtrationThe mixture is filtered
  4. washthe solid rinsed with dimethylformamide
  5. customthe filtrate evaporated at 40° C. under reduced pressure
  6. dissolutionThe residue is dissolved in 50 ml
  7. washof ether and washed three times with 5% sodium bicarbonate solution
  8. dry with materialwith saturated salt solution, dried over magnesium sulfate
  9. customevaporated
  10. customThe residue is crystallized from a minimum of methanol
  11. additionby adding ether
  12. customThe product is recrystallized from methanol-ether

Sources & evidence

ORD record
ord-1f5d59b4abf1414fb990374f4f7270ef
Source dataset
uspto-grants-1977_08
Patent number
US04043994

Reaction notes

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