N-(tert-butoxycarbonyl)glycine → HCID 58292592, compound

HRID 1798313Notes

Reaction equation

HRID 1798313 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:37][C:38]1[S:42][C:41]([O:43][C:44]2[CH:45]=[C:46]([CH3:60])[C:47]3[CH:51]([CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54])[O:50][B:49]([OH:58])[C:48]=3[CH:59]=2)=[N:40][N:39]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:37][C:38]1[S:42][C:41]([O:43][C:44]2[CH:45]=[C:46]([CH3:60])[C:47]3[CH:51]([CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54])[O:50][B:49]([OH:58])[C:48]=3[CH:59]=2)=[N:40][N:39]=1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58292641Ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292592HCID 58292592, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-tert-butoxy carbonyl-glycine (1.05 g, 6 mmol) in DMF (15 mL) was added HATU (2.85 g, 7.5 mmol), ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (1.74 g, 5 mmol) and DIEA (1.73 mL). The mixture was stirred at room overnight. The mixture was concentrated to afford the target molecule.

Workup

  1. concentrationThe mixture was concentrated
  2. customto afford the target molecule

Sources & evidence

ORD record
ord-1e22eb2b0e6049beaca1f4fc58c0bd57
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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