Triethylamine → HCID 131710220, compound

HRID 1076427Notes

Reaction equation

HRID 1076427 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:19]([O:21]N1C(=O)CCC1=O)=O)[CH2:10][S:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])[CH3:3].[NH2:29][C@H:30]([C:33]([NH:35][C@H:36]([C:41]([NH:43][C@H:44]([C:49]([NH:51][C@H:52]([C:55]([NH:57][C@H:58]([C:62]([OH:64])=[O:63])[C@@H:59]([CH3:61])[OH:60])=[O:56])[CH2:53][OH:54])=[O:50])[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:42])[CH2:37][C:38](=[O:40])[NH2:39])=[O:34])[CH2:31][OH:32].C(N(CC)CC)C>CN(C)C=O>[NH:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:9]([C:19]([NH:29][C@H:30]([C:33]([NH:35][C@H:36]([C:41]([NH:43][C@H:44]([C:49]([NH:51][C@H:52]([C:55]([NH:57][C@H:58]([C:62]([OH:64])=[O:63])[C@@H:59]([CH3:61])[OH:60])=[O:56])[CH2:53][OH:54])=[O:50])[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:42])[CH2:37][C:38](=[O:40])[NH2:39])=[O:34])[CH2:31][OH:32])=[O:21])[CH2:10][S:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13670098HCID 13670098, compoundHCID 131710221HCID 131710221, compound

Product 1

HCID 131710220HCID 131710220, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5.3 g (13 mmols) of BOC-Cys(Bzl)-OSU and 7.4 g (10 mmols) of H-Ser-Asn-Leu-Ser-Thr-OH, 1.93TFA are dissolved in 75 ml of dimethylformamide. From a solution of 150 mmols of triethylamine in 100 ml of dimethylformamide, 18.1 ml (27.2 mmols) are added dropwise while stirring until the reaction mixture shows a pH of 6.4 on moist indicator paper. The solution is stirred for 3 days at room temperature, then evaporated to dryness in a high vacuum. The residue is stirred twice with 250 ml of ethyl acetate and three times with a mixture of 100 ml of ethyl acetate and 20 ml of 5% citric acid solution, filtered, and dried at 40°C under reduced pressure. Melting point: 184°-185°C; [α]D20 -13° (c = 2 in dimethylformamide); Rf6 = 0.45.

Workup

  1. stirringThe solution is stirred for 3 days at room temperature
  2. customevaporated to dryness in a high vacuum
  3. stirringThe residue is stirred twice with 250 ml of ethyl acetate and three times with a mixture of 100 ml of ethyl acetate and 20 ml of 5% citric acid solution
  4. filtrationfiltered
  5. customdried at 40°C under reduced pressure

Sources & evidence

ORD record
ord-948b49f455f2454392d84e4bf43d4f45
Source dataset
uspto-grants-1976_05
Patent number
US03956260

Reaction notes

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