Acetic Acid → HCID 70000419, compound

HRID 1634851Notes

Reaction equation

HRID 1634851 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].[CH2:17]([O:19][C:20](=[O:43])[C@H:21]([NH:26][C:27](=[O:42])[C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH2:39][CH2:38][CH:37]([CH:40]=O)[CH2:36][CH2:35]2)=[CH:30][CH:29]=1)[CH2:22][CH:23]([CH3:25])[CH3:24])[CH3:18].C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C1COCC1>[CH2:17]([O:19][C:20](=[O:43])[C@@H:21]([NH:26][C:27](=[O:42])[C:28]1[CH:29]=[CH:30][C:31]([N:34]2[CH2:35][CH2:36][CH:37]([CH2:40][NH:1][CH2:2][C@H:3]([OH:4])[C:5]3[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=3)[CH2:38][CH2:39]2)=[CH:32][CH:33]=1)[CH2:22][CH:23]([CH3:25])[CH3:24])[CH3:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 88097363HCID 88097363, compound

Product 1

HCID 70000419HCID 70000419, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of N-[5-(2-amino-1-{R}-hydroxyethyl)-2-hydroxyphenyl]-methane-sulfonamide (0.098 g, 0.4 mmol), (2R)-2-{[4-(4-(formyl)piperidin-1-yl)benzoyl]amino}4-methylpentanoic acid ethyl ester (0.4 mmol) and glacial acetic acid (0.023 g, 0.4 mmol) in 5 mL of methanol-THF (4:1, v/v) was stirred for 1 hour over 4A molecular sieves. In one portion sodium cyanoborohydride (0.026 g, 0.4 mmol) was added and the mixture stirred overnight at ambient temperature. The sieves were filtered and the filtrate was preabsorbed on silica gel. The solids were purified by flash chromatography (CH2Cl2—CH3OH, 20:1). to give the product (0.072 g).

Workup

  1. filtrationThe sieves were filtered
  2. customthe filtrate was preabsorbed on silica gel
  3. customThe solids were purified by flash chromatography (CH2Cl2—CH3OH, 20:1)

Sources & evidence

ORD record
ord-c7d60b066fca4dc5880ba5a9c1abe651
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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