Tetrahydrofuran → HCID 131715025, compound

HRID 980413Notes

Reaction equation

HRID 980413 reaction equation
[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:19]([OH:21])=[O:20])[CH3:18])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:29][C@H:30]([C:35]([CH2:37][Cl:38])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33].Cl.O1CCCC1>CC(C)=O.CCOCC>[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:19]([NH:29][C@H:30]([C:35]([CH2:37][Cl:38])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:20])[CH3:18])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[NH:1]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:19]([OH:21])=[O:20])[CH3:18])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 16219556HCID 16219556, compound2×HCID 131715026HCID 131715026, compound

Product 2

HCID 131715025HCID 131715025, compoundHCID 131715026HCID 131715026, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Boc-Phe-Gly-Ala-LeuCH2Cl was prepared by coupling Boc-Phe-Gly-Ala-OH (11.8 g, 30 mmol) to H-LeuCH2Cl.HCl (6.06 g, 30 mmol) using a mixed anhydride procedure. A mixed anhydride of Boc-Phe-Gly-Ala-OH was prepared in a solution of 300 mL of tetrahydrofuran and 25 mL of acetone, and then H-LeuCH2Cl HCl was added in acetone. The resulting crude product, 17.6 g, was dissolved in ether, treated with carbon, and filtered. Product Boc-Phe-Gly-Ala-LeuCH2Cl crystallized from ether (10.0 g).

Workup

  1. additiontreated with carbon
  2. filtrationfiltered
  3. customProduct Boc-Phe-Gly-Ala-LeuCH2Cl crystallized from ether (10.0 g)

Sources & evidence

ORD record
ord-c8b677167e63484aa1e6c461d8560173
Source dataset
uspto-grants-1987_01
Patent number
US04636492

Reaction notes

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