4-Thiazoleacetic acid, 2-amino-, ethyl ester → HCID 86614382, compound

HRID 1660862Notes

Reaction equation

[C:1]1([CH3:23])[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([N:10]2[C:15]3[CH:16]=[C:17]([C:20](O)=[O:21])[CH:18]=[CH:19][C:14]=3[O:13][CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:2]=1.[NH2:24][C:25]1[S:26][CH:27]=[C:28]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:29]=1>>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][C:28]1[N:29]=[C:25]([NH:24][C:20]([C:17]2[CH:18]=[CH:19][C:14]3[O:13][CH2:12][CH2:11][N:10]([S:7]([C:3]4[CH:2]=[C:1]([CH3:23])[CH:6]=[CH:5][CH:4]=4)(=[O:8])=[O:9])[C:15]=3[CH:16]=2)=[O:21])[S:26][CH:27]=1)[CH3:35]

Participants

Reactant 2

HCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl ester

HCID 66788666HCID 66788666, compound

Product 1

HCID 86614382HCID 86614382, compound

Procedure

The title compound, MS (ISP)=472.1 (M−H)−, was produced as described in example 1, steps 1-6. Step 3 was performed using 3-methylbenzenesulfonyl chloride, furnishing 4-(toluene-3-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester, which was hydrolyzed in step 4, leading to 4-(toluene-3-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid. This was reacted with ethyl 2-amino-4-thiazoleacetate in step 5 and yielded (2-{[4-(toluene-3-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-thiazol-4-yl)-acetic acid ethyl ester, which was hydrolyzed in step 6.

Sources & evidence

ORD record: ord-124d6067efc745d697eae5894721ac57
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030308B2

Reaction notes

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