Triphosgene → HCID 67995835, compound

HRID 1615183Notes

Reaction equation

HRID 1615183 reaction equation
COC1C=CC([C@@H](NCCC2(O)CCC3(OCC(C)(C)CO3)CC2)CC)=CC=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[CH3:41][O:42][C:43]1[CH:48]=[CH:47][C:46]([C@@H:49]([N:52]2[CH2:57][CH2:56][C:55]3([CH2:69][CH2:68][C:60]4(OCC(C)(C)C[O:61]4)[CH2:59][CH2:58]3)[O:54][C:53]2=[O:70])[CH2:50][CH3:51])=[CH:45][CH:44]=1>>[CH3:41][O:42][C:43]1[CH:48]=[CH:47][C:46]([C@@H:49]([N:52]2[CH2:57][CH2:56][C:55]3([CH2:69][CH2:68][C:60](=[O:61])[CH2:59][CH2:58]3)[O:54][C:53]2=[O:70])[CH2:50][CH3:51])=[CH:45][CH:44]=1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 67995425HCID 67995425, compoundHCID 67996053HCID 67996053, compound

Product 1

HCID 67995835HCID 67995835, compound

Procedure

The title compound is prepared from 9-{2-[(S)-1-(4-methoxy-phenyl)-propylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol and triphosgene following a procedure analogous to that described in Step 4 of Intermediate 2; the crude product, a mixture of the title compound and 3-[(S)-1-(4-methoxy-phenyl)-propyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one, obtained after that is treated as described in Step 10 of Intermediate 2 to convert the intermediate to the title compound as well. Yield: 62% of theory; LC (method 6): tR=1.33 min; Mass spectrum (ESI+): m/z=332 [M+H]+.

Workup

  1. customobtained after
  2. additionthat is treated

Sources & evidence

ORD record
ord-1a2074662f3d469da1865aeb0b2acf98
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

Loading…