Sodium Bicarbonate → HCID 90370153, compound

HRID 2176041Notes

Reaction equation

HRID 2176041 reaction equation
[CH3:1][CH2:2][CH:3]([NH:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:44]=[CH:45][CH:46]=1)[C:11]([NH:13][C:14]1[S:15][C:16]2[CH2:43][CH2:42][CH2:41][CH2:40][C:17]=2[C:18]=1[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=2)=[CH:24][CH:23]=1)=[O:20])=[O:12])[CH2:4][CH3:5].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:61][N:62]([CH2:72][CH:73]=O)[C:63](=[O:71])[CH2:64][CH2:65][C:66]([O:68][CH2:69][CH3:70])=[O:67].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH2:69]([O:68][C:66](=[O:67])[CH2:65][CH2:64][C:63]([N:62]([CH3:61])[CH2:72][CH2:73][N:6]([CH2:7][C:8]1[CH:9]=[C:10]([CH:44]=[CH:45][CH:46]=1)[C:11]([NH:13][C:14]1[S:15][C:16]2[CH2:43][CH2:42][CH2:41][CH2:40][C:17]=2[C:18]=1[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:38][CH:39]=2)=[CH:24][CH:23]=1)=[O:20])=[O:12])[CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:71])[CH3:70]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 90370232HCID 90370232, compoundHCID 90370256HCID 90370256, compound2×

Product 1

HCID 90370153HCID 90370153, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1.00 g of methyl 4-{2-[4-({[2-({3-[(pentan-3-ylamino)methyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoate, 1.00 g of sodium triacetoxyborohydride, 0.50 mL of acetic acid and 20 mL of methylene chloride was added 473 mg of ethyl 4-[methyl(2-oxoethyl)amino]-4-oxobutanoate, followed by stirring for 1 hour at room temperature. 498 mg of sodium triacetoxyborohydride and 237 mg of ethyl 4-[methyl(2-oxoethyl)amino]-4-oxobutanoate were further added to the reaction mixture, followed by stirring for 2 hours at room temperature. An aqueous sodium hydrogen carbonate solution was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate), thereby obtaining 1.19 g of methyl 4-(2-{4-[({2-[(3-{[{2-[(4-ethoxy-4-oxobutanoyl)(methyl)amino]ethyl}(pentan-3-yl)amino]methyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}ethyl)benzoate.

Workup

  1. stirringby stirring for 2 hours at room temperature
  2. extractionfollowed by extraction with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-4dfe907d7c4a464db433a97e4a1f8f4a
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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