Hydrochloric Acid → HCID 86601671, compound

HRID 269602Notes

Reaction equation

HRID 269602 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:26][C:27]([NH:29][CH2:30][C@H:31]([O:107][Si](C(C)(C)C)(C)C)[CH2:32][C@H:33]([NH:99][C:100]([O:102][C:103]([CH3:106])([CH3:105])[CH3:104])=[O:101])[C:34]([NH:36][C@@H:37]([CH2:48][C:49]1[CH:50]=[C:51]([C:63]2[CH:68]=[CH:67][C:66]([O:69][CH2:70][C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)=[C:65]([CH2:77][C@H:78]([NH:88][C:89]([O:91][CH2:92][C:93]3[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=3)=[O:90])[C:79]([O:81]CC[Si](C)(C)C)=[O:80])[CH:64]=2)[CH:52]=[CH:53][C:54]=1[O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])=[O:35])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC)(=O)C.Cl>C1COCC1.CN(C=O)C>[CH2:92]([O:91][C:89]([NH:88][C@@H:78]([CH2:77][C:65]1[CH:64]=[C:63]([C:51]2[CH:52]=[CH:53][C:54]([O:55][CH2:56][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[C:49]([CH2:48][C@@H:37]([C:38]([O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[O:39])[NH:36][C:34](=[O:35])[C@@H:33]([NH:99][C:100]([O:102][C:103]([CH3:104])([CH3:106])[CH3:105])=[O:101])[CH2:32][C@@H:31]([OH:107])[CH2:30][NH:29][C:27]([O:26][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:28])[CH:50]=2)[CH:68]=[CH:67][C:66]=1[O:69][CH2:70][C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)[C:79]([OH:81])=[O:80])=[O:90])[C:93]1[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86601672HCID 86601672, compound

Product 1

HCID 86601671HCID 86601671, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.8 ml of 1N tetrabutylammonium fluoride in THF are added dropwise to a solution of 800 mg (0.6 mmol) of benzyl 2(S)-[5-benzyloxycarbonylamino-2(S)-tert-butoxycarbonylamino-4(R)-(tert-butyldimethylsilyloxy)pentanoylamino]-3-{4,4′-bisbenzyloxy-3′-[2(S)-benzyloxycarbonylamino-2-(2-trimethylsilylethoxycarbonyl)ethyl]biphenyl-3-yl}propionate (Example 16A) in 26 ml of absolute DMF at RT. After 25 min at RT, the mixture is cooled to 0° C. and a large amount of ice-water is added. Ethyl acetate and a little 1N hydrochloric acid solution are immediately added; the organic phase is dried with magnesium sulfate, concentrated and dried under high vacuum for 1 h. The crude product is reacted without further purification.

Workup

  1. dry with materialthe organic phase is dried with magnesium sulfate
  2. concentrationconcentrated
  3. customdried under high vacuum for 1 h
  4. customThe crude product is reacted without further purification

Sources & evidence

ORD record
ord-65843cef1adc4386a92523a7b726e753
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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