1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Z-Gly-Gly-Gly-Glu(OtBu)-Thr(tBu)-OtBu

HRID 2260549Notes

Reaction equation

HRID 2260549 reaction equation
[NH2:1][C@H:2]([C:12]([NH:14][C@H:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:16]([CH3:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[NH:30]([C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44])[CH2:31][C:32]([NH:34][CH2:35][C:36]([NH:38][CH2:39][C:40](O)=[O:41])=[O:37])=[O:33].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[NH:30]([C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44])[CH2:31][C:32]([NH:34][CH2:35][C:36]([NH:38][CH2:39][C:40]([NH:1][C@H:2]([C:12]([NH:14][C@H:15]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[C@@H:16]([CH3:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:41])=[O:37])=[O:33]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 297872N-((Phenylmethoxy)carbonyl)glycylglycylglycineHCID 131719230H-Glu(OtBu)-Thr(tBu)-OtBu

Product 1

HCID 131719229Z-Gly-Gly-Gly-Glu(OtBu)-Thr(tBu)-OtBu

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

H-Glu(OtBu)-Thr(tBu)-OtBu (1.27 g, 3.05 mmol) and Z-Gly-Gly-Gly-OH (0.99 g, 3.05 mmol) were dissolved in DMF (20 ml). To the solution were added HOBT (453 mg, 3.35 mmol) and WSC (643 mg, 3.35 mmol). The mixture was stirred for 8 hours at 20° C. The reaction mixture was concentrated, which was suspended in 0.2M aqueous solution of citric acid (70 ml), followed by extraction with ethyl acetate (100 ml, 70 ml). The ethyl acetate layers were combined and washed with a 10% (w/v) aqueous solution of ammonium chloride, 5% (w/v) aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous saline solution, successively, which was dried over anhydrous sodium sulfate, followed by concentration. To the concentrate was added ether-hexane. Resulting precipitates were collected by filtration to afford Z-Gly-Gly-Gly-Glu(OtBu)-Thr(tBu)-OtBu (Z-P-2) as a while powdery product (1.87 g, 85%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionfollowed by extraction with ethyl acetate (100 ml, 70 ml)
  3. washwashed with a 10% (w/v) aqueous solution of ammonium chloride, 5% (w/v) aqueous solution of sodium hydrogencarbonate, water
  4. dry with materiala saturated aqueous saline solution, successively, which was dried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration
  6. additionTo the concentrate was added ether-hexane
  7. customResulting
  8. customprecipitates
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-313fb782064846cb88925ab0a77a23d8
Source dataset
uspto-grants-1995_12
Patent number
US05478808

Reaction notes

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