Triethylamine → HCID 178501839, compound

HRID 355523Notes

Reaction equation

HRID 355523 reaction equation
[NH:1]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C@H:2]([C:9]([OH:11])=O)[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:47][C@H:48]([C:64]([NH:66][C@H:67]([C:77]([C:79]([O:81][CH3:82])=[O:80])=[O:78])[CH2:68][O:69][CH2:70][C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)=[O:65])[CH2:49][C:50]1[CH:55]=[CH:54][C:53]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[CH:52][CH:51]=1.FC(C(O)=O)(F)F.CCN(CC)CC>CN(C=O)C>[NH:1]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C@H:2]([C:9]([NH:47][C@H:48]([C:64]([NH:66][C@H:67]([C:77]([C:79]([O:81][CH3:82])=[O:80])=[O:78])[CH2:68][O:69][CH2:70][C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)=[O:65])[CH2:49][C:50]1[CH:51]=[CH:52][C:53]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[CH:54][CH:55]=1)=[O:11])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 131720922Tyr(OBn)-Ser(OBn)-CO2Me.TFAHCID 178523877HCID 178523877, compound

Product 1

HCID 178501839HCID 178501839, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Cbz-His (1.00 g, 3.47 mmol) in DMF (15 mL) at 0° C. was added HOBT (0.64 g, 4.16 mmol) and DCC (0.86 g, 4.16 mmol). Tyr(OBn)-Ser(OBn)-CO2Me.TFA (from Step 2 above, 2.0 g, 3.47 mmol) was added followed by Et3N (0.58 mL, 4.16 mmol). The mixture was allowed to warm to room temperature and stirred overnight. The mixture was filtered and the filtrate was diluted with CHCl3, washed twice with saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated. Flash chromatography (2-5% MeOH/CHCl3) gave 2.14 g of the title compound as a white solid, mp 175°-176°C.; FAB-MS 734 (m+1);

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with CHCl3
  3. washwashed twice with saturated aqueous NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-458595e4e1664e45ba0bd5b2313ec1c8
Source dataset
uspto-grants-1998_11
Patent number
US05830868

Reaction notes

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