Triphosgene → HCID 67995942, compound

HRID 1615182Notes

Reaction equation

HRID 1615182 reaction equation
C(C1C=CC([C@@H](NCCC2(O)CCC3(OCC(C)(C)CO3)CC2)C)=CC=1)(C)(C)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[C:42]([C:46]1[CH:51]=[CH:50][C:49]([C@@H:52]([N:54]2[CH2:59][CH2:58][C:57]3([CH2:71][CH2:70][C:62]4(OCC(C)(C)C[O:63]4)[CH2:61][CH2:60]3)[O:56][C:55]2=[O:72])[CH3:53])=[CH:48][CH:47]=1)([CH3:45])([CH3:44])[CH3:43]>>[C:42]([C:46]1[CH:51]=[CH:50][C:49]([C@@H:52]([N:54]2[CH2:59][CH2:58][C:57]3([CH2:60][CH2:61][C:62](=[O:63])[CH2:70][CH2:71]3)[O:56][C:55]2=[O:72])[CH3:53])=[CH:48][CH:47]=1)([CH3:43])([CH3:44])[CH3:45]

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 67995836HCID 67995836, compoundHCID 67996114HCID 67996114, compound

Product 1

HCID 67995942HCID 67995942, compound

Procedure

The title compound is prepared from 9-{2-[(S)-1-(4-tert-butyl-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-tert-butyl-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: 65% of theory; LC (method 6): tR=1.51 min; Mass spectrum (ESI+): m/z=344 [M+H]+.

Workup

  1. customobtained after
  2. additionthat is treated

Sources & evidence

ORD record
ord-b769837f6f5646fbab8300e233bd26bb
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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