ethyl 1-[N-(3,4-methylenedioxyphenylcarbonyl) amino]cyclohexanecarboxylate → 1-[N-(4-methoxybenzenesulfonyl)amino]cyclohexanecarboxylic acid

HRID 1953446Notes

Reaction equation

HRID 1953446 reaction equation
C1OC2C=CC(C(NC3(C(OCC)=O)CCCCC3)=O)=CC=2O1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:35][C:36]2([C:42]([O:44]CC3C=CC=CC=3)=[O:43])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1>>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:35][C:36]2([C:42]([OH:44])=[O:43])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 23297898ethyl 1-[N-(3,4-methylenedioxyphenylcarbonyl) amino]cyclohexanecarboxylateHCID 23297905phenylmethyl 1-[N-(4-methoxybenzenesulfonyl)amino]cyclohexanecarboxylate

Product 1

HCID 9741571-[N-(4-methoxybenzenesulfonyl)amino]cyclohexanecarboxylic acidYield 57.4%

Procedure

Subsequently, the same procedure as in Reference Example 4 was repeated except that the ethyl 1-[N-(3,4-methylenedioxyphenylcarbonyl)amino]cyclohexanecarboxylate was replaced by 1.0 g (2.5 mmol) of phenylmethyl 1-[N-(4-methoxybenzenesulfonyl)amino]cyclohexanecarboxylate, whereby 450 mg of the captioned 1-[N-(4-methoxybenzenesulfonyl)amino]cyclohexanecarboxylic acid was obtained in a yield of 26%.

Sources & evidence

ORD record
ord-1ee8674f153d4f5d9835038632c0034c
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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