Bicarbonate Ion → HCID 178493269, compound

HRID 630417Notes

Reaction equation

HRID 630417 reaction equation
[OH:1][C:2]([C:36]1[S:37][CH:38]=[CH:39][CH:40]=1)([C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([CH2:27][CH:28]=O)=[CH:21][C:20]=2[Cl:30])=[O:17])[CH3:13])[CH2:8][CH2:7]1)=[O:4].C([O-])(=O)C.[Si:45]([O:52][C@H:53]([C:56]1[CH:65]=[CH:64][C:63]([OH:66])=[C:62]2[C:57]=1[CH:58]=[CH:59][C:60](=[O:67])[NH:61]2)[CH2:54][NH3+:55])([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46].C(NCCNC(C)C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-]>CO>[OH:1][C:2]([C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)([C:36]1[S:37][CH:38]=[CH:39][CH:40]=1)[C:3]([O:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([N:12]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([CH2:27][CH2:28][NH:55][CH2:54][C@H:53]([O:52][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:46])[CH3:47])[C:56]3[CH:65]=[CH:64][C:63]([OH:66])=[C:62]4[C:57]=3[CH:58]=[CH:59][C:60](=[O:67])[NH:61]4)=[CH:21][C:20]=2[Cl:30])=[O:17])[CH3:13])[CH2:10][CH2:11]1)=[O:4]

Participants

7

Reactant 5

HCID 769Bicarbonate IonHCID 77628N,N'-DiisopropylethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 67145275[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-2-(8-hydroxy-2-oxo-1H-quinolin-5-yl)ethyl]azanium acetateHCID 178493270HCID 178493270, compound2×

Product 1

HCID 178493269HCID 178493269, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of trans-4-[(3-{[2-chloro-5-methoxy-4-(2-oxoethyl)phenyl]amino}-3-oxopropyl)(methyl)amino]cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 123; 173 mg, 0.16 mmol) in methanol (1.73 mL) was added (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethanaminium acetate (prepared according to preparation 8 from US20060035931) (78 mg, 0.2 mmol), diisopropylethylendiamine (0.03 mL, 0.2 mmol) and sodium triacetoxyborohydride (108 mg, 0.51 mmol). The reaction mixture was stirred for 2.5 hours at room temperature. At 0° C. the mixture was added into a 20 mL of bicarbonate 4%, then the crude was extracted with ethyl acetate, washed with water and brine, dried and the solvent was removed under reduced pressure. The crude obtained was purified by column chromatography with silica gel, eluting with methylen chloride/methanol (9:1) to give the title compound as a yellow solid (52%).

Workup

  1. extractionthe crude was extracted with ethyl acetate
  2. washwashed with water and brine
  3. customdried
  4. customthe solvent was removed under reduced pressure
  5. customThe crude obtained
  6. customwas purified by column chromatography with silica gel
  7. washeluting with methylen chloride/methanol (9:1)

Sources & evidence

ORD record
ord-74e2ef5a35414ab893d66b6f6590f53c
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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