Sodium Sulfite → HCID 67319917, compound

HRID 626647Notes

Reaction equation

HRID 626647 reaction equation
CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:22]C)C=C4)N(CC2)C1.CS(N)(=O)=O.C(OC([NH:71][CH2:72][CH2:73][CH2:74][CH2:75][C@H:76]([NH:84][C:85]([NH:87][C@@H:88]1[CH2:103][C:102]2=[CH:104][CH:105]=[C:99]([CH:100]=[CH:101]2)[O:98]CC=C[CH2:94][O:93][CH2:92][C@H:91]([CH:106]([CH3:108])[CH3:107])[NH:90][C:89]1=[O:109])=[O:86])[C:77]([O:79]C(C)(C)C)=[O:78])=O)(C)(C)C.S([O-])([O-])=O.[Na+].[Na+].[C:116]([OH:120])([CH3:119])([CH3:118])C.O>C(OC(NCCCC[C@H](NC(N[C@@H]1CC2=CC=C(C=C2)OCC(O)C(O)COC[C@H](C(C)C)NC1=O)=O)C(OC(C)(C)C)=O)=O)(C)(C)C>[NH2:71][CH2:72][CH2:73][CH2:74][CH2:75][C@H:76]([NH:84][C:85]([NH:87][C@@H:88]1[CH2:103][C:102]2=[CH:101][CH:100]=[C:99]([CH:105]=[CH:104]2)[O:98][CH2:119][CH:116]([OH:120])[CH:118]([OH:22])[CH2:94][O:93][CH2:92][C@H:91]([CH:106]([CH3:107])[CH3:108])[NH:90][C:89]1=[O:109])=[O:86])[C:77]([OH:79])=[O:78]

Participants

7

Reactant 5

HCID 24437Sodium SulfiteHCID 72879MethanesulfonamideHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine2×HCID 714019492-Methylpropan-2-ol--water (1/1)HCID 86655972HCID 86655972, compound

Product 1

HCID 67319917HCID 67319917, compound

Reagents, catalysts & solvents 1

HCID 70943705HCID 70943705, compoundCatalyst

Conditions

Temperature
0 °C

Procedure

tert-Butyl(S)-6-tert-butoxycarbonylamino-2-[3-((9S,12R)-4,5-dihydroxy-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-yl)ureido]hexanoate 8 mg (9.7 μmol) of (DHQ)2PHAL (hydroquinine 1,4-phthalazinediyl diether) were added to a mixture of 541 mg (387 mmol) of AD-Mix-alpha and 3 mg (7.7 μmol) of potassium osmate in tert-butanol/water (1:1, v/v). After a clear solution had formed, the reaction mixture was cooled to 0° C., 41 mg (425 μmol) of methanesulfonamide were added, and the mixture was stirred at this temperature for 15 min. Then 250 mg (387 μmol) of tert-butyl(S)-6-tert-butoxycarbonylamino-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),4,14(18),15-tetraen-12-yl)ureido]hexanoate (step B) were added, and the mixture was warmed to RT and left to stand over the weekend. 195 mg (1.55 mmol) of sodium sulfite were then added, and the mixture was stirred at RT for 1 h. The reaction mixture was extracted with ethyl acetate, and the organic phase was dried over Na2SO4, filtered and concentrated in a rotary evaporator. The residue was purified by preparative HPLC. 164 mg of the title compound were obtained.

Workup

  1. customAfter a clear solution had formed
  2. temperaturethe mixture was warmed to RT
  3. waitleft
  4. stirringthe mixture was stirred at RT for 1 h
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. dry with materialthe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in a rotary evaporator
  9. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-de45876691f1419299a04b4cd1bb042f
Source dataset
uspto-grants-2016_04
Patent number
US09309207B2

Reaction notes

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