Dicyclohexylcarbodiimide → HCID 131710180, compound

HRID 1606838Notes

Reaction equation

HRID 1606838 reaction equation
FC1C(O)=C(F)C(F)=C(F)C=1F.[NH:13]([C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[C@H:14]([C:19]([NH:21][CH2:22][C:23]([OH:25])=O)=[O:20])[CH2:15][C:16](=[O:18])[NH2:17].[NH2:36][C@H:37]([C:39]([NH:41][C@H:42]([C:52]([NH:54][C@H:55]([C:64]([NH:66][C@H:67]([C:77]([NH:79][C@H:80]([C:83]([NH:85][C@H:86]([C:88]([O:90][C:91]([CH3:94])([CH3:93])[CH3:92])=[O:89])[CH3:87])=[O:84])[CH2:81][OH:82])=[O:78])[CH2:68][CH2:69][C:70](=[O:76])[O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:65])[CH2:56][C:57](=[O:63])[O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:53])[CH2:43][CH2:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:40])[CH3:38].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:13]([C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[C@H:14]([C:19]([NH:21][CH2:22][C:23]([NH:36][C@H:37]([C:39]([NH:41][C@H:42]([C:52]([NH:54][C@H:55]([C:64]([NH:66][C@H:67]([C:77]([NH:79][C@H:80]([C:83]([NH:85][C@H:86]([C:88]([O:90][C:91]([CH3:92])([CH3:93])[CH3:94])=[O:89])[CH3:87])=[O:84])[CH2:81][OH:82])=[O:78])[CH2:68][CH2:69][C:70](=[O:76])[O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:65])[CH2:56][C:57](=[O:63])[O:58][C:59]([CH3:60])([CH3:61])[CH3:62])=[O:53])[CH2:43][CH2:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:40])[CH3:38])=[O:25])=[O:20])[CH2:15][C:16](=[O:18])[NH2:17]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 53645221HCID 53645221, compoundHCID 131710178HCID 131710178, compound

Product 1

HCID 131710180HCID 131710180, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2.45 g. (13.3 mmoles) of pentafluorophenol, 1.31 g. (4.02 mmoles) of Z-Asn-Gly-OH (see Example 1) and 5.4 g. (4.02 mmoles) of H-27-32-OtBu are dissolved in 24 ml. of dry DMF, thereafter the solution is cooled to 0°C, and 0.915 g. (4.43 mmoles) of DCC are added to it. The reaction mixture is stirred at 0°C for 0.5 hours and at room temperature for 2.5 hours. The separated DCU is filtered off, and the filtrate is evaporated to dryness. The solid residue is triturated with ethyl acetate, filtered, and washed with hot ethyl acetate. 4.12 g. (89 %) of Z-25-32-OtBu are obtained. M.p.: 200°-201°C; Rf3 = 0.6; [α]D = -13.9° (c = 1, in DMF).

Workup

  1. filtrationThe separated DCU is filtered off
  2. customthe filtrate is evaporated to dryness
  3. customThe solid residue is triturated with ethyl acetate
  4. filtrationfiltered
  5. washwashed with hot ethyl acetate

Sources & evidence

ORD record
ord-0b0e8817099e4efd9e986086000de0e5
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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