Acetic Acid → HCID 44331443, compound

HRID 1634848Notes

Reaction equation

HRID 1634848 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].C([O:24][C:25](=[O:55])[C@@H:26]([NH:34][C:35]([NH:37][C:38]1[CH:43]=[CH:42][C:41]([S:44]([N:47]2[CH2:52][CH2:51][CH:50]([CH:53]=O)[CH2:49][CH2:48]2)(=[O:46])=[O:45])=[CH:40][CH:39]=1)=[O:36])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)C1C=CC=CC=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[OH:4][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)[CH2:2][NH:1][CH2:53][CH:50]1[CH2:51][CH2:52][N:47]([S:44]([C:41]2[CH:42]=[CH:43][C:38]([NH:37][C:35]([NH:34][C@@H:26]([CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:25]([OH:55])=[O:24])=[O:36])=[CH:39][CH:40]=2)(=[O:46])=[O:45])[CH2:48][CH2:49]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 86758802HCID 86758802, compound

Product 1

HCID 44331443HCID 44331443, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-[5-(2-amino-1-{R}-hydroxyethyl)-2-hydroxyphenyl]-methane-sulfonamide (0.320 g, 1.3 mmol), (2S)-2-{3-[4-(4-formyl-piperidine-1-sulfonyl)-phenyl]-ureido}-3-phenyl-propionic acid benzyl ester (1.3 mmol) and glacial acetic acid (0.074 g, 1.3 mmol) in 5 mL methanol was stirred for 1 hour over 4A molecular sieves. In one portion sodium cyanoborohydride (0.086 g, 1.3 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, 19:1). to give 0.12 g of the product.

Workup

  1. filtrationThe sieves were filtered
  2. customthe filtrate was preabsorbed on silica gel
  3. customThe solids were purified by flash chromatography (CH2Cl2—CH3OH, 19:1)

Sources & evidence

ORD record
ord-0b73df514d0247ae8d538eff33235bc5
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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