Triphosgene → HCID 67995958, compound

HRID 1615190Notes

Reaction equation

HRID 1615190 reaction equation
FC(F)C1C=CC([C@@H](NCCC2(O)CCC3(OCC(C)(C)CO3)CC2)C)=CC=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[F:41][CH:42]([F:70])[C:43]1[CH:48]=[CH:47][C:46]([C@@H:49]([N:51]2[CH2:56][CH2:55][C:54]3([CH2:68][CH2:67][C:59]4(OCC(C)(C)C[O:60]4)[CH2:58][CH2:57]3)[O:53][C:52]2=[O:69])[CH3:50])=[CH:45][CH:44]=1>>[F:70][CH:42]([F:41])[C:43]1[CH:48]=[CH:47][C:46]([C@@H:49]([N:51]2[CH2:56][CH2:55][C:54]3([CH2:68][CH2:67][C:59](=[O:60])[CH2:58][CH2:57]3)[O:53][C:52]2=[O:69])[CH3:50])=[CH:45][CH:44]=1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 67995914HCID 67995914, compoundHCID 67996049HCID 67996049, compound

Product 1

HCID 67995958HCID 67995958, compound

Procedure

The title compound is prepared from 9-{2-[(S)-1-(4-difluoromethyl-phenyl)-ethylamino]-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-difluoromethyl-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one, obtained thereafter is treated as described in Step 10 of Intermediate 2 to convert the intermediate to the title compound as well. Yield: 58% of theory; LC (method 8): tR=1.10 min; Mass spectrum (ESI+): m/z=338 [M+H]+.

Workup

  1. customobtained
  2. additionthereafter is treated

Sources & evidence

ORD record
ord-d64302bebda84e77ad6d5a6ff2707d45
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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