Water → HCID 86622974, compound

HRID 1712225Notes

Reaction equation

HRID 1712225 reaction equation
C(N(CC)CC)C.ClC(O[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=O.C[O:22][C:23](C)(C)C.[CH2:27]([O:29][CH:30]([O:32][C:33]1([CH3:88])[CH:45]([OH:46])[CH:44]=[CH:43][CH:42]([CH3:47])[CH:41](/[C:48](/[CH3:79])=[CH:49]/[CH:50]=[CH:51]/[C:52]([CH3:78])([O:70][Si:71]([CH2:76][CH3:77])([CH2:74][CH3:75])[CH2:72][CH3:73])[CH2:53][CH:54]2[O:69][CH:55]2[CH:56]([CH3:68])[CH:57]([O:60][Si:61]([CH2:66][CH3:67])([CH2:64][CH3:65])[CH2:62][CH3:63])[CH2:58][CH3:59])[O:40][C:38](=[O:39])[CH2:37][CH:36]([O:80][Si:81]([CH2:86][CH3:87])([CH2:84][CH3:85])[CH2:82][CH3:83])[CH2:35][CH2:34]1)[CH3:31])[CH3:28].[OH2:89]>CN(C)C1C=CN=CC=1>[CH2:27]([O:29][CH:30]([O:32][C:33]1([CH3:88])[CH:45]([O:46][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:44]=[CH:43][CH:42]([CH3:47])[CH:41](/[C:48](/[CH3:79])=[CH:49]/[CH:50]=[CH:51]/[C:52]([CH3:78])([O:70][Si:71]([CH2:76][CH3:77])([CH2:74][CH3:75])[CH2:72][CH3:73])[CH2:53][CH:54]2[O:69][CH:55]2[CH:56]([CH3:68])[CH:57]([O:60][Si:61]([CH2:64][CH3:65])([CH2:62][CH3:63])[CH2:66][CH3:67])[CH2:58][CH3:59])[O:40][C:38](=[O:39])[CH:37]([C:23]([OH:22])=[O:89])[CH:36]([O:80][Si:81]([CH2:86][CH3:87])([CH2:84][CH3:85])[CH2:82][CH3:83])[CH2:35][CH2:34]1)[CH3:31])[CH3:28]

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 821294-Nitrophenyl chloroformateHCID 86622972HCID 86622972, compound

Product 1

HCID 86622974HCID 86622974, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
25 °C

Procedure

Under a nitrogen atmosphere and warming to hold the outside temperature at 25° C., 2.29 g (18.8 mmol) of 4-(dimethylamino)pyridine, 10.9 mL (78.2 mmol) of triethylamine and 8.13 g (39.1 mmol) of p-nitrophenyl chloroformate were added to a t-butyl methyl ether (217 mL) solution of 14.5 g (15.6 mmol) of (8E,12E,14E)-6-(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-3,16,21-tris(triethylsiloxy)-18,19-epoxytricosa-8,12,14-trien-11-olide, following which stirring was carried out for 7 hours 30 minutes with maintaining the external temperature at 25° C. Water (145 mL) was then added to the reaction mixture, after which the organic phase was separated, yielding a t-butyl methyl ether solution of the title compound.

Workup

  1. temperatureUnder a nitrogen atmosphere and warming
  2. customat 25° C.
  3. customafter which the organic phase was separated

Sources & evidence

ORD record
ord-daf7d16290e64946a440140687c99f79
Source dataset
uspto-grants-2010_09
Patent number
US07790887B2

Reaction notes

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