Triphosgene → HCID 67996093, compound

HRID 1615191Notes

Reaction equation

HRID 1615191 reaction equation
CC1(C)OCC2(CCC(CCN[C@H](C3C=CC=CC=3)CC)(O)CC2)C[O:3]1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.CC1(C)OC[C:43]2([CH2:63][CH2:62][C:46]3([O:51][C:50](=[O:52])[N:49]([C@H:53]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[CH2:54][CH3:55])[CH2:48][CH2:47]3)[CH2:45][CH2:44]2)CO1>>[C:56]1([C@@H:53]([N:49]2[CH2:48][CH2:47][C:46]3([CH2:45][CH2:44][C:43](=[O:3])[CH2:63][CH2:62]3)[O:51][C:50]2=[O:52])[CH2:54][CH3:55])[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 67995629HCID 67995629, compoundHCID 70498595HCID 70498595, compound

Product 1

HCID 67996093HCID 67996093, compound

Procedure

The title compound is prepared from 3,3-dimethyl-9-{2-[(S)-1-phenyl-propylamino]-ethyl}-2,4-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 12,12-dimethyl-3-[(S)-1-phenyl-propyl]-1,11,13-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: 56% of theory; LC (method 8): tR=1.20 min; Mass spectrum (ESI+): m/z=302 [M+H]+.

Workup

  1. customobtained
  2. additionthereafter is treated

Sources & evidence

ORD record
ord-cf48cd20ed0a4ccf86a1b6f5a15af8cb
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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