6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid → 6-[[(2,3-Dihydro-5-benzofuranyl)hydroxyacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

HRID 2323103Notes

Reaction equation

HRID 2323103 reaction equation
[C:49](=[O:50])([OH:51])[O-:52].[CH2:27]([O:28][C:29]([Cl:30])=[O:31])[CH:32]([CH3:33])[CH3:34].[CH3:15][Si:16]([CH:17]([Si:18]([CH3:19])([CH3:20])[CH3:21])[C:22]([NH2:23])=[O:24])([CH3:25])[CH3:26].[CH3:55][CH2:56][N:57]([CH2:58][CH3:59])[CH2:60][CH3:61].[NH2:35][CH:36]1[CH:37]2[S:38][C:39]([CH3:47])([CH3:48])[CH:40]([C:44](=[O:45])[OH:46])[N:41]2[C:42]1=[O:43].[Na+:53].[O:1]1[CH2:2][CH2:3][c:4]2[c:5]1[cH:6][cH:7][c:8]([CH:10]([C:11](=[O:12])[OH:13])[OH:14])[cH:9]2.[O:62]1[CH2:63][CH2:64][CH2:65][CH2:66]1.[OH2:54]>>[O:1]1[CH2:2][CH2:3][c:4]2[c:5]1[cH:6][cH:7][c:8]([CH:10]([C:11](=[O:13])[NH:35][CH:36]1[CH:37]3[S:38][C:39]([CH3:47])([CH3:48])[CH:40]([C:44](=[O:45])[OH:46])[N:41]3[C:42]1=[O:43])[OH:14])[cH:9]2

Participants

10

Reactant 9

HCID 1626-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidHCID 769Bicarbonate IonHCID 923Sodium ionHCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 11708267BistrimethylsilylacetamidHCID 233358212-(2,3-Dihydrobenzofuran-5-yl)-2-hydroxyacetic acid

Product 1

HCID 227484976-[[(2,3-Dihydro-5-benzofuranyl)hydroxyacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Sources & evidence

ORD record
ord-eb90aa9e577b4b8cb68192fa9521737b
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (10/10)

Reaction notes

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