Acetic Acid → DCCI HOBt

HRID 2419496Notes

Reaction equation

HRID 2419496 reaction equation
N(C(OCC1C=CC=CC=1)=O)[C@H](C(NCC(NCC(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(O)=O)CCCCNC(OCC1C=CC=CC=1)=O)=O)CCC(=O)OCC1C=CC=CC=1)=O)COCC1C=CC=CC=1)=O)[C@@H](C)OCC1C=CC=CC=1)=O)CCSC)=O)CC1C=CC=CC=1)=O)=O)=O)CC1C=CC(O)=CC=1.[CH:113]1[CH:114]=[CH:115][C:116]2[N:121]([OH:122])[N:120]=[N:119][C:117]=2[CH:118]=1.[CH2:123]1[CH2:128][CH2:127][CH:126]([N:129]=[C:130]=[N:131][CH:132]2[CH2:137][CH2:136][CH2:135][CH2:134][CH2:133]2)[CH2:125][CH2:124]1.CC(O)=O>CN(C=O)C.C1(O)C=CC=CC=1>[CH2:135]1[CH2:134][CH2:133][CH:132]([N:131]=[C:130]=[N:129][CH:126]2[CH2:127][CH2:128][CH2:123][CH2:124][CH2:125]2)[CH2:137][CH2:136]1.[CH:113]1[CH:114]=[CH:115][C:116]2[N:121]([OH:122])[N:120]=[N:119][C:117]=2[CH:118]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 131711187HCID 131711187, compound

Product 1

HCID 21712060DCCI HOBt

Reagents, catalysts & solvents 2

HCID 996PhenolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Z-Tyr-Gly-Gly-Phe-Met-Thr(Bzl)-Ser(Bzl)-Glu(OBzl)-Lys(Z)-OH (VI) (0.311g, 0.2 mmol) was dissolved in DMF (2 ml) and the solution was cooled to 0° C. HOBt (0.065g, 0.4 mmol) was added, followed by DCC (0.045g, 0.22 mmol). The mixture was stirred for 1 hour at 0° C and for 1 hour at room temperature. It was then added to a solution of the above docosapeptide amine dissolved in molten phenol. The mixture was stirred for 3 days at room temperature. It was poured slowly to a stirred, cold (0° C), solution of 0.5% AcOH (200 ml). The precipitated solid was filtered and washed with H2O and EtOH. The crude product was triturated three times with boiling MeOH, centrifuged, and dried. Precipitation from DMF/MeOH provided 0.20g (50%); mp 275°-279° C dec. The material was without further characterization subjected to complete protecting group removal with liquid HF.

Workup

  1. stirringThe mixture was stirred for 3 days at room temperature
  2. filtrationThe precipitated solid was filtered
  3. washwashed with H2O and EtOH
  4. customThe crude product was triturated three times with boiling MeOH
  5. customcentrifuged, and dried
  6. customPrecipitation from DMF/MeOH
  7. customprovided 0.20g (50%)
  8. customgroup removal with liquid HF

Sources & evidence

ORD record
ord-6fc58503beee44c6bfc8550af8c9a6b5
Source dataset
uspto-grants-1978_08
Patent number
US04105652

Reaction notes

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