Triphosgene → HCID 67996029, compound

HRID 1615142Notes

Reaction equation

HRID 1615142 reaction equation
FC1C=C(F)C=CC=1[C@@H](NCCC1(O)CCC2(OCC(C)(C)CO2)CC1)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[F:40][C:41]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:42]=1[C@@H:48]([N:50]1[CH2:55][CH2:54][C:53]2([CH2:67][CH2:66][C:58]3(OCC(C)(C)C[O:59]3)[CH2:57][CH2:56]2)[O:52][C:51]1=[O:68])[CH3:49]>>[F:40][C:41]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:42]=1[C@@H:48]([N:50]1[CH2:55][CH2:54][C:53]2([CH2:67][CH2:66][C:58](=[O:59])[CH2:57][CH2:56]2)[O:52][C:51]1=[O:68])[CH3:49]

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 67995737HCID 67995737, compoundHCID 67996352HCID 67996352, compound

Product 1

HCID 67996029HCID 67996029, compound

Procedure

The title compound is prepared from 9-{2-[(S)-1-(2,4-difluoro-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-(2,4-difluoro-phenyl)-ethyl]-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: 30% of theory; LC (method 6): tR=1.10 min; Mass spectrum (ESI+): m/z=324 [M+H]+.

Workup

  1. customobtained after
  2. additionthat is treated

Sources & evidence

ORD record
ord-2605127038c247ada4d21a19ace77079
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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