Benzyl mercaptan → HCID 68993960, compound

HRID 1799659Notes

Reaction equation

HRID 1799659 reaction equation
C1(CS)C=CC=CC=1.BrCCCCCCCCO.C(SCCCCCCCCO)C1C=CC=CC=1.[C:36]1([CH2:42][S:43]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][OH:54])(=[O:45])=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C1(CS(CCCCCCCC(O)=O)(=O)=O)C=CC=CC=1.Cl.Cl.[CH2:77]([O:84][C:85](=[O:93])[CH2:86][C@@H:87]([NH2:92])[CH2:88][N:89]([CH3:91])[CH3:90])[C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1>>[CH2:77]([O:84][C:85](=[O:93])[CH2:86][C@@H:87]([NH:92][C:53](=[O:54])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][S:43]([CH2:42][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)(=[O:44])=[O:45])[CH2:88][N:89]([CH3:90])[CH3:91])[C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1

Participants

7

Reactant 6

HCID 7509Benzyl mercaptanHCID 1626071-Octanol, 8-bromo-HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66874848HCID 66874848, compoundHCID 66875121HCID 66875121, compoundHCID 68994214HCID 68994214, compound

Product 1

HCID 68993960HCID 68993960, compound

Procedure

The title compound, m/e=427.4 ([M+H]+), was produced in analogy with example 59, steps 1 to 5. Thus, phenyl-methanethiol was alkylated in step 1 with 8-bromo-1-octanol, leading to 8-benzylsulfanyl-octan-1-ol, which was oxidized in step 2 to 8-phenylmethanesulfonyl-octan-1-ol. This was oxidized in step 3 to 8-phenylmethanesulfonyl-octanoic acid, then coupled in step 4 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-4-dimethylamino-3-(8-(phenylmethanesulfonyl)-octanoylamino)-butyric acid benzyl ester, which was hydrogenated in step 5.

Sources & evidence

ORD record
ord-a241412f80c64b569df781a70266e74b
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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