Triphosgene → HCID 67996134, compound

HRID 1615184Notes

Reaction equation

HRID 1615184 reaction equation
CC1(C)COC2(CCC(CCN[C@H](C3C=CC=CC=3)C)(O)CC2)OC1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.CC1(C)CO[C:42]2([CH2:61][CH2:60][C:45]3([O:50][C:49](=[O:51])[N:48]([C@H:52]([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[CH3:53])[CH2:47][CH2:46]3)[CH2:44][CH2:43]2)[O:41]C1>>[C:54]1([C@@H:52]([N:48]2[CH2:47][CH2:46][C:45]3([CH2:60][CH2:61][C:42](=[O:41])[CH2:43][CH2:44]3)[O:50][C:49]2=[O:51])[CH3:53])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 67996181HCID 67996181, compoundHCID 67996252HCID 67996252, compound

Product 1

HCID 67996134HCID 67996134, compound

Procedure

The title compound is prepared from 3,3-dimethyl-9-{2-[(S)-1-phenyl-ethylamino]-ethyl}-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 12,12-dimethyl-3-[(S)-1-phenyl-ethyl]-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: 49% of theory; LC (method 6): tR=1.06 min; Mass spectrum (ESI+): m/z=288 [M+H]+.

Workup

  1. customobtained
  2. additionthereafter is treated

Sources & evidence

ORD record
ord-dfe5a0cb3a0e451a8c8264eca0f1ff2e
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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