Triethylamine → HCID 178455966, compound

HRID 2254597Notes

Reaction equation

HRID 2254597 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:16]([NH:18][C@H:19]([C:39]([O:41][CH3:42])=[O:40])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:38])[NH:25][S:26]([C:29]1[C:36]([CH3:37])=[CH:35][C:33]([CH3:34])=[CH:32][C:30]=1[CH3:31])(=[O:28])=[O:27])=[O:17])[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4].[NH:43]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C@H:44]([C:49](O)=[O:50])[C@H:45]([CH2:47][CH3:48])[CH3:46].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C(N(CC)CC)C>CN(C=O)C.O1CCOCC1>[NH:43]([C:52]([O:54][C:55]([CH3:57])([CH3:56])[CH3:58])=[O:53])[C@H:44]([C:49]([NH:1][CH2:2][C:3]([NH:5][C@H:6]([C:16]([NH:18][C@H:19]([C:39]([O:41][CH3:42])=[O:40])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:38])[NH:25][S:26]([C:29]1[C:30]([CH3:31])=[CH:32][C:33]([CH3:34])=[CH:35][C:36]=1[CH3:37])(=[O:27])=[O:28])=[O:17])[CH2:7][O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:4])=[O:50])[C@H:45]([CH2:47][CH3:48])[CH3:46]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 178501465HCID 178501465, compound

Product 1

HCID 178455966HCID 178455966, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

The Boc group of product (XIII) was removed by the same method as described in regard to compound (XI) to give 0.40 g (0.63 mmol) of HCl.H-Gly-Ser(Bzl)-Arg(Mts)-OMe. It was then dissolved in a mixed solvent of 5.4 ml of rectified DMF and 5.4 ml of dioxane together with the equimolar amount (0.14 g) of Boc-Ile-OH. The resulting solution was stirred at 0° C. for 10 minutes and then 0.21 ml of DPPA and 0.20 ml of triethylamine were added. The mixture was stirred at room temperature for 24 hours. The solution thus obtained was freed from any acidic and alkaline materials in the same manner as described in regard to compounds (XII) and (XIII). After drying, 0.28 g of Boc-Ile-Gly-Ser(Bzl)-Arg(Mts)-OMe was obtained.

Workup

  1. stirringThe mixture was stirred at room temperature for 24 hours
  2. customThe solution thus obtained
  3. customAfter drying

Sources & evidence

ORD record
ord-7180a1c6994545ca8795c7e99c50664e
Source dataset
uspto-grants-1993_08
Patent number
US05236903

Reaction notes

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