N-(tert-butoxycarbonyl)glycine → HCID 9827681, compound

HRID 2414632Notes

Reaction equation

HRID 2414632 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].O.[OH:14][N:15]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(O[C:39]([CH:41]1[CH2:46][NH:45][CH2:44][CH2:43][N:42]1[S:47]([C:50]1[CH:55]=[CH:54][C:53]([O:56][CH2:57][C:58]#[C:59][CH3:60])=[CH:52][CH:51]=1)(=[O:49])=[O:48])=[O:40])C>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]([N:45]1[CH2:44][CH2:43][N:42]([S:47]([C:50]2[CH:51]=[CH:52][C:53]([O:56][CH2:57][C:58]#[C:59][CH3:60])=[CH:54][CH:55]=2)(=[O:49])=[O:48])[CH:41]([C:39](=[O:40])[NH:15][OH:14])[CH2:46]1)=[O:12])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 54175880HCID 54175880, compound

Product 1

HCID 9827681HCID 9827681, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.14 g (0.8 mmol) of N-(tert-butoxycarbonyl)glycine dissolved in 3 mL of DMF was added 0.13 g (0.963 mmol) of 1-hydroxybenzotriazole hydrate (HOBT) followed by 0.203 g (1.06 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC). The resulting mixture was stirred at room temperature for 1 h and 0.191 g (0.522 mmol) of 1-(4-but-2-ynyloxy-benzenesulfonyl)-piperazine-2-carboxylic acid ethyl ester in 3 mL of DMF was added dropwise. After stirring the reaction for 14 h the solution was diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:1) to provide 0.26 g (95%) of the sulfonamide, ethyl 4-{2-[(tert-butoxycarbonyl)amino]acetyl)-1-{[4-(2-butynyloxy)phenyl]sulfonyl}-2-piperazinecarboxylate, as a clear oil. Electrospray Mass Spec: 524.2 (M+H)+

Workup

  1. stirringAfter stirring
  2. customthe reaction for 14 h the solution
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-1842947511de409980406188d928cc36
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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