HCID 58762829, compound → 2-(4-(TERT-BUTOXYCARBONYL(METHYL)AMINO) PHENYL)ACETIC ACID

HRID 858058Notes

Reaction equation

HRID 858058 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](=[O:38])[NH:16][C:17]2[C:18](=[O:37])[N:19]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[F:36])[C:20](=[O:28])[N:21]([CH2:24][CH:25]3[CH2:27][CH2:26]3)[C:22]=2[NH2:23])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:40]([O:44][C:45](=[O:75])[N:46]([C:48]1[CH:53]=[CH:52][C:51]([CH2:54][C:55](=[O:74])NC2C(=O)N(CC3C=CC=CC=3F)C(=O)NC=2N)=[CH:50][CH:49]=1)[CH3:47])([CH3:43])([CH3:42])[CH3:41]>>[C:1]([O:5][C:6](=[O:39])[N:7]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15](=[O:38])[NH:16][C:17]2[C:18](=[O:37])[N:19]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[F:36])[C:20](=[O:28])[N:21]([CH2:24][CH:25]3[CH2:26][CH2:27]3)[C:22]=2[NH2:23])=[CH:12][CH:13]=1)[CH3:40])([CH3:4])([CH3:2])[CH3:3].[C:40]([O:44][C:45]([N:46]([CH3:47])[C:48]1[CH:49]=[CH:50][C:51]([CH2:54][C:55]([OH:74])=[O:5])=[CH:52][CH:53]=1)=[O:75])([CH3:41])([CH3:42])[CH3:43]

Participants

4

Reactant 2

HCID 58762829HCID 58762829, compoundHCID 58762834(4-{[6-Amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-carbamic acid tert-butyl ester

Product 2

HCID 107303972-(4-(TERT-BUTOXYCARBONYL(METHYL)AMINO) PHENYL)ACETIC ACIDHCID 58762840(4-{[6-Amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-methyl-carbamic acid tert-butyl ester

Procedure

Prepared by the same procedure as described for the preparation of (4-{[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-carbamic acid tert-butyl ester (example 1, step 5) except that (4-{[6-amino-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-methyl-carbamic acid tert-butyl ester was used in place of (4-{[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-carbamic acid tert-butyl ester. Purified by chromatography using silica eluted with 3% v/v methanol in chloroform to give (4-{[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-methyl-carbamic acid tert-butyl ester as a colorless solid foam (63% yield from [4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-acetic acid).

Workup

  1. customPrepared by the same procedure
  2. customPurified by chromatography
  3. washeluted with 3% v/v methanol in chloroform

Sources & evidence

ORD record
ord-10682bec2b8b4f7daa9668f3df637933
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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