1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → {[1-(4-Phenyl-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

HRID 1893301Notes

Reaction equation

HRID 1893301 reaction equation
[CH3:1]CN=C=NCCCN(C)C.OC(C(F)(F)F)=O.[C:19]1([CH:25]2[CH2:30][CH2:29][CH:28]([NH:31][CH:32]3[CH2:35][NH:34]C3)[CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:36]([O:40][C:41]([NH:43][CH2:44][C:45]([OH:47])=O)=[O:42])([CH3:39])([CH3:38])[CH3:37]>>[C:36]([O:40][C:41](=[O:42])[NH:43][CH2:44][C:45](=[O:47])[NH:34][CH:35]1[CH2:32][N:31]([CH:28]2[CH2:27][CH2:26][CH:25]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:30][CH2:29]2)[CH2:1]1)([CH3:37])([CH3:38])[CH3:39]

Participants

4

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 86646680(4-Phenyl-cyclohexyl)-azetidin-3-ylamine TFA Salt

Product 1

HCID 59541886{[1-(4-Phenyl-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

Procedure

The title compound was prepared as a white solid from the EDCI coupling of (4-phenyl-cyclohexyl)-azetidin-3-ylamine TFA salt (as prepared in the previous step) and tert-butoxycarbonylamino-acetic acid (Aldrich) using the procedure described in Step F of Example 1.

Sources & evidence

ORD record
ord-844e9dea20684b7286f25156050ebac7
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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