Citric Acid → HCID 59334939, compound

HRID 1517971Notes

Reaction equation

[C:1]([O:5][C:6]([CH2:8][N:9]([S:27]([C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[CH:31]=1)(=[O:29])=[O:28])[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19](=[O:22])[NH:20][CH3:21])[CH2:14][CH:13]2[C:23](OC)=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].C(OCC)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[Cl:37][C:32]1[CH:31]=[C:30]([S:27]([N:9]([CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([C:19](=[O:22])[NH:20][CH3:21])[CH2:14][CH:13]3[CH2:23][OH:24])(=[O:29])=[O:28])[CH:35]=[C:34]([Cl:36])[CH:33]=1

Participants

Conditions

Temperature: 0 °C

Procedure

110 mg methyl 5-[tert-butoxycarbonylmethyl-(3,5-dichloro-phenylsulphonyl)-amino]-1-methylcarbamoyl-2,3-dihydro-1H-indole-3-carboxylate are dissolved in 3 ml of tetrahydrofuran, cooled to 0° C., combined with 4.2 mg lithium borohydride and stirred for 1 hour. Then the mixture is allowed to come up to ambient temperature and stirred overnight. Then it is divided between ethyl acetate and ice water, the pH is adjusted to 4 by the addition of citric acid and the phases are separated. The organic phase is washed with water and saturated sodium chloride solution, dried on magnesium sulphate and freed from the solvents in vacuo. The residue is chromatographed on silica gel (ethyl acetate).

Workup

customto come up to ambient temperature
stirringstirred overnight
customthe phases are separated
washThe organic phase is washed with water and saturated sodium chloride solution
customdried on magnesium sulphate
customThe residue is chromatographed on silica gel (ethyl acetate)

Sources & evidence

ORD record: ord-17c5d1184c314e32932732860efe92bb
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232312B2

Reaction notes

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