Triethylamine → HCID 131711702, compound

HRID 2052274Notes

Reaction equation

HRID 2052274 reaction equation
[NH2:1][C@H:2]([C:6]([NH:8][C@H:9]([C:14]([NH:16][C@@H:17]([C:24]([NH2:26])=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:10][C:11](=[O:13])[OH:12])=[O:7])[CH2:3][CH2:4][CH3:5].Cl.[NH:28]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:29]([C:40](ON1C(=O)CCC1=O)=[O:41])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1.C(N(CC)CC)C>CN(C=O)C>[NH:28]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:29]([C:40]([NH:1][C@H:2]([C:6]([NH:8][C@H:9]([C:14]([NH:16][C@@H:17]([C:24]([NH2:26])=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:10][C:11](=[O:12])[OH:13])=[O:7])[CH2:3][CH2:4][CH3:5])=[O:41])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98767tert-Butyl (S)-(2-((2,5-dioxo-1-pyrrolidinyl)oxy)-1-(1H-indol-3-ylmethyl)-2-oxoethyl)carbamateHCID 131711703HCID 131711703, compound

Product 1

HCID 131711702HCID 131711702, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.50 g (3.74 mmoles) of H-Nva-Asp-D-Phg-NH2.HCl are reacted with 1.50 g (3.74 mmoles) of BOC-Trp-OSu in 30 ml of DMF in the presence of 1.05 ml (7.5 mmoles) of triethylamine. Next day the reaction mixture is evaporated in vacuo, the residue is admixed with water, and the mixture is filtered. The obtained crude product, weighing 2.36 g, is recrystallized from 300 ml of 80% ethanol. 1.54 g (66.2%) of BOC-Trp-Nva-Asp-D-Phg-NH2 are obtained; m.p.: 240° C. (decomposition), Rf5 :0.35, [α]D :-60.5° (c: 1.0, in dimethyl formamide).

Workup

  1. customNext day the reaction mixture is evaporated in vacuo
  2. filtrationthe mixture is filtered
  3. customThe obtained crude product
  4. customis recrystallized from 300 ml of 80% ethanol

Sources & evidence

ORD record
ord-a158547135d84688860622d6ba4f49db
Source dataset
uspto-grants-1980_01
Patent number
US04183909

Reaction notes

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