Anisole → HCID 131714620, compound

HRID 980417Notes

Reaction equation

HRID 980417 reaction equation
[NH:1]([C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:27]([NH:29][C@H:30]([C:35]([CH2:37][Cl:38])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:28])[CH2:18][O:19]CC1C=CC=CC=1)=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(OC)C=CC=CC=1>>[NH:1]([C:39]([O:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:40])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:27]([NH:29][C@H:30]([C:35]([CH2:37][Cl:38])=[O:36])[CH2:31][CH:32]([CH3:33])[CH3:34])=[O:28])[CH2:18][OH:19])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:1][C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:27]([NH:29][C@H:30]([C:35]([CH2:37][Cl:38])=[O:36])[CH2:31][CH:32]([CH3:33])[CH3:34])=[O:28])[CH2:18][OH:19])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 131714621HCID 131714621, compound

Product 2

HCID 131714620HCID 131714620, compoundYield 21.1%HCID 131715030HCID 131715030, compound

Procedure

Z-Phe-Gly-Ser-LeuCH2Cl was prepared by the following procedure. First, Z-Phe-Gly-Ser(OCH2C6H5)LeuCH2Cl (0.98 g, 14.4 mmol) was deblocked by treatment with 15 mL of anhydrous HF and 1 mL of anisole (Procedure K) to yield 0.69 g of H-Phe-Gly-Ser-LeuCH2Cl.HF. This intermediate (0.59 g, 12.4 mmol) was then coupled with carbobenzoxychloride substantially according to the procedure of Procedure K to yield 0.4 g of Z-Phe-Gly-Ser-LeuCH2Cl (m.p. 146°-146.5°) after crystallization from ethyl acetate/hexane.

Sources & evidence

ORD record
ord-69c69efc624b4f0495f2e6629b2d2605
Source dataset
uspto-grants-1987_01
Patent number
US04636492

Reaction notes

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