Hydrochloric Acid → HCID 60024438, compound

HRID 1920625Notes

Reaction equation

HRID 1920625 reaction equation
C(B(O)O)C(C)C.[C:8]1([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C@@H:15]([CH2:44][C:45]2[CH:50]=[C:49]([O:51][CH3:52])[C:48]([O:53][CH3:54])=[C:47]([O:55][CH3:56])[CH:46]=2)[C:16]([NH:18][C@@H:19]([CH:41]([CH3:43])[CH3:42])[C:20]([NH:22][C@H:23]([B:28]2[O:36][C@H]3[C@](C)([C@H]4C[C@@H](C3)C4(C)C)[O:29]2)[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:21])=[O:17])[CH:9]=1.Cl>CO.CCCCCC>[C:8]1([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C@@H:15]([CH2:44][C:45]2[CH:46]=[C:47]([O:55][CH3:56])[C:48]([O:53][CH3:54])=[C:49]([O:51][CH3:52])[CH:50]=2)[C:16]([NH:18][C@@H:19]([CH:41]([CH3:43])[CH3:42])[C:20]([NH:22][C@H:23]([B:28]([OH:36])[OH:29])[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:21])=[O:17])[CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2734395(2-Methylpropyl)boronic acidHCID 10283913HCID 10283913, compound

Product 1

HCID 60024438HCID 60024438, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8058HexaneSolvent2×

Procedure

i-BuB(OH)2 is added to a mixture of (S)-2-[(S)-2-(Biphenyl-3-ylamino)-3-(3,4,5-trimethoxy-phenyl)-propionylamino]-3-methyl-N-[(R)-3-methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-butyl]-butyramide, methanol (4.3 mL), hexane (4.3 mL) and 1N HCl (1.45 mL). The reaction mixture is stirred for 2 h at rt and then diluted with methanol (8 mL) and hexane (8 mL). The two layers are separated. The methanol layer is washed twice with hexane, diluted with CH2Cl2, washed with H2O, dried (Na2SO4), filtered and concentrated. The residue is dissolved in CH2Cl2 and purified by silica gel (20 g) column chromatography (CH2Cl2/MeOH, 80/20) to afford the title compound as a pale yellow foam.

Workup

  1. customThe two layers are separated
  2. washThe methanol layer is washed twice with hexane
  3. additiondiluted with CH2Cl2
  4. washwashed with H2O
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe residue is dissolved in CH2Cl2
  9. custompurified by silica gel (20 g) column chromatography (CH2Cl2/MeOH, 80/20)

Sources & evidence

ORD record
ord-70c89592644c40d589392bfaa726eba1
Source dataset
uspto-grants-2012_05
Patent number
US08173128B2

Reaction notes

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