Triphosgene → HCID 67995731, compound

HRID 1615186Notes

Reaction equation

HRID 1615186 reaction equation
CC1(C)COC2(CCC(CCN[C@H](C3C4C(=CC=CC=4)C=CC=3)C)(O)CC2)OC1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.CC1(C)CO[C:46]2([CH2:69][CH2:68][C:49]3([O:54][C:53](=[O:55])[N:52]([C@H:56]([C:58]4[C:67]5[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=5)[CH:61]=[CH:60][CH:59]=4)[CH3:57])[CH2:51][CH2:50]3)[CH2:48][CH2:47]2)[O:45]C1>>[C:58]1([C@@H:56]([N:52]2[CH2:51][CH2:50][C:49]3([CH2:68][CH2:69][C:46](=[O:45])[CH2:47][CH2:48]3)[O:54][C:53]2=[O:55])[CH3:57])[C:67]2[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=2)[CH:61]=[CH:60][CH:59]=1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 67995784HCID 67995784, compoundHCID 70497606HCID 70497606, compound

Product 1

HCID 67995731HCID 67995731, compound

Procedure

The title compound is prepared from 3,3-dimethyl-9-{2-[(S)-1-naphthalen-1-yl-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-naphthalen-1-yl-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: 62% of theory; LC (method 6): tR=1.33 min; Mass spectrum (ESI+): m/z=338 [M+H]+.

Workup

  1. customobtained
  2. additionthereafter is treated

Sources & evidence

ORD record
ord-2083e1ab39f24ef793a01748fa195037
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

Loading…