Tetrahydrofuran → (3-Benzyloxycarbonylamino-2-oxo-2h-pyridin-1-yl)acetic acid tert-butyl ester

HRID 58313Notes

Reaction equation

HRID 58313 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[NH:10][C:11]1(O)[CH:16]=[CH:15][CH:14]=[N:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:21]([O:25][C:26](=[O:29])[CH2:27]Br)([CH3:24])([CH3:23])[CH3:22].C1C[O:33]CC1>>[CH2:1]([O:8][C:9]([NH:10][C:11]1[C:12](=[O:33])[N:13]([CH2:27][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:29])[CH:14]=[CH:15][CH:16]=1)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 131736991Benzyl-3-hydroxypyridin-3-yl-carbamate

Product 1

HCID 70027044(3-Benzyloxycarbonylamino-2-oxo-2h-pyridin-1-yl)acetic acid tert-butyl ester

Conditions

Temperature
0 °C

Procedure

16.2 g of benzyl-3-hydroxypyridin-3-yl-carbamate (66.4 mmol) are suspended in 900 mL of absolute THF and cooled to 0° C. under argon atmosphere and 2.92 g of NaH (60% in mineral oil, 73.1 mmol, 1.1 eq) are added. To the resulting solution after the end of gas emission (ca. 15 min) 13.7 mL of bromoacetic acid tert-butylester (89.7 mmol, 1.35 eq) are added. It is stirred still for 15 minutes at 0° C. and subsequently at RT overnight. The reaction mixture is filtered and the filtrate is concentrated in dryness. The residue is taken up in 5 mL of ethyl acetate and treated with ca. 50 mL of diethylether and the resulting suspension is precipitated in the refrigerator overnight. The crystals are filtered off and washed with a little amount of ether.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in dryness
  3. additiontreated with ca. 50 mL of diethylether
  4. customthe resulting suspension is precipitated in the refrigerator overnight
  5. filtrationThe crystals are filtered off
  6. washwashed with a little amount of ether

Sources & evidence

ORD record
ord-77cc0f1f25cd41bc8105cd54ea1fc650
Source dataset
uspto-grants-2016_09
Patent number
US09434763B2

Reaction notes

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