Benzyl mercaptan → HCID 131724472, compound

HRID 1882754Notes

Reaction equation

HRID 1882754 reaction equation
[NH:1]([C:18]([O:20][CH2:21][CH:22]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[C@H:2]([C:15](O)=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:50]([SH:57])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[NH:1]([C:18]([O:20][CH2:21][CH:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:29]2[C:34]1=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:19])[C@H:2]([C:15]([S:57][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([CH3:14])([CH3:12])[CH3:13])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 10868DicyclohexylcarbodiimideHCID 10895791Fmoc-L-Tyr(tBu)-OH

Product 1

HCID 131724472HCID 131724472, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4.6 g (10.0 mmol) Fmoc-Tyr(But)-OH, 2.1 g (10.1 mmol) dicylohexylcarbodiimide (DCC), 1.26 g (10.1 mmol) benzylmercaptan and 0.12 g DMAP were reacted in DCM as described by Ho and Ngu (J. Org. Chem. 58:2315 (1993), which is incorporated herein by reference). After workup, Fmoc-Tyr(But)-S—CH2C6H5 was isolated and, upon reduction of the thioester by stirring with triethylsilane in the presence of 10% Pd on carbon and purification by flash chromatography, gave a 81% yield of Fmoc-Tyr(But)-H. The NMR and mass of the product were in accordance with the expected range.

Sources & evidence

ORD record
ord-5c20e65500d541caa084af592d5e930f
Source dataset
uspto-grants-2004_07
Patent number
US06759384B1

Reaction notes

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