Acetic Acid → HCID 10283807, compound

HRID 1634822Notes

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].[CH3:17][O:18][C:19](=[O:51])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][NH:29][C:30]([NH:32][C:33]2[CH:38]=[CH:37][C:36]([S:39]([N:42]3[CH2:47][CH2:46][CH:45]([CH:48]=O)[CH2:44][CH2:43]3)(=[O:41])=[O:40])=[CH:35][CH:34]=2)=[O:31])=[C:24]([F:50])[CH:23]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>>[F:50][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[CH2:28][NH:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][C:36]([S:39]([N:42]2[CH2:43][CH2:44][CH:45]([CH2:48][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)[CH2:46][CH2:47]2)(=[O:40])=[O:41])=[CH:35][CH:34]=1)=[O:31])[O:21][CH2:20][C:19]([O:18][CH3:17])=[O:51]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 5003444Sodium cyanoborohydride

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

HCID 86758800HCID 86758800, compound

Product 1

HCID 10283807HCID 10283807, compoundYield 56.9%

Procedure

The title compound was prepared from N-[5-(2-amino-1-{R}-hydroxyethyl)-2-hydroxyphenyl]-methanesulfonamide (0.128 g, 0.52 mmol), (4-{3-[4-(4-formyl-piperidine-1-sulfonyl)-phenyl]-ureidomethyl}-3-fluoro-phenoxy)-acetic acid methyl ester (0.5 mmol), glacial acetic acid (0.03 mL, 0.5 mmol) and sodium cyanoborohydride (0.031 g, 0.5 mmol) according to the general procedure used for example 84 (Step E) to give the final product (0.21 g).

Sources & evidence

ORD record: ord-c0f39c7ffe1a4a72abb4961023360033
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506901B2

Reaction notes

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