N-(tert-butoxycarbonyl)glycine → HCID 72558433, compound

HRID 661603Notes

Reaction equation

HRID 661603 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C@@H:11]([OH:21])[C@H:12]([NH:15][C:16]([CH:18]([Cl:20])[Cl:19])=[O:17])[CH2:13][F:14])=[CH:9][CH:10]=1)(=[O:4])=[O:3].C([NH:29][CH2:30][C:31](O)=[O:32])(OC(C)(C)C)=O>>[Cl:19][CH:18]([Cl:20])[C:16]([NH:15][CH:12]([CH2:13][F:14])[CH:11]([O:21][C:31](=[O:32])[CH2:30][NH2:29])[C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=1)=[O:17]

Participants

3

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 114811Florfenicol

Product 1

HCID 72558433HCID 72558433, compoundYield 80%

Procedure

By following the general procedures II and III using 12.9 g of florfenicol and 6.9 g of N-Boc glycine, the prodrug (13.2 g, 80% yield) was obtained as white powder after the crude solids were dried under reduced pressure at 50° C. for 6 days; H1-NMR (DMSO-d6), δ=3.2 ppm (m, 3H), 3.9 ppm (s, 2H), 4.3-4.7 ppm (m, 3H), 6.1 ppm (s, 1H), 6.8 ppm (s, 1H), 7.7 ppm (d, 2H), 7.9 ppm (d, 2H), 8.6 ppm (br, 3H), 9.4 ppm (d, 1H).

Workup

  1. customthe prodrug (13.2 g, 80% yield) was obtained as white powder after the crude solids
  2. customwere dried under reduced pressure at 50° C. for 6 days

Sources & evidence

ORD record
ord-513739ef14e0451eaf532363adad8234
Source dataset
uspto-grants-2011_12
Patent number
US08084643B2

Reaction notes

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