Acetic Acid → HCID 59656745, compound

HRID 1170805Notes

Reaction equation

HRID 1170805 reaction equation
C([O:8][CH2:9][CH:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:11]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12])C1C=CC=CC=1.CC(O)=O>CO>[OH:8][CH2:9][CH:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[C:11]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 59656748HCID 59656748, compound

Product 1

HCID 59656745HCID 59656745, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-butyl-3-(benzyloxy)-1-morpholino-1-oxopropan-2-ylcarbamate (31) (1.4 g, 4.0 mmol, 1.0 equiv.) was added to a 250 mL RBF followed by MeOH (40 mL). The reaction flask was flushed with N2 (g) and charged with 10% Pd/C (290 mg). The flask was equipped with 2H2 (g) balloons and stirred at rt for 30 min. AcOH (230 μL, 4.0 mmol, 1.0 equiv) was then added and the reaction was allowed to stir for 10 h. The solution was filtered through a pad of celite, washing with additional MeOH (200 mL). The solution was concentrated on a rotary evaporator, and dried under vacuum to give 1.2 g of crude material. The residue was purified by flash column chromatography (100% EtOAc) to give 970 mg (88%) of 32 as a colorless oil which crystallized to a white solid. Rf=0.26 (100% EtOAc); mp=45-47° C.; IR (film) 3418, 3315, 2972, 2927, 2859, 1706, 1631, 1444, 1166 cm−1; 1H NMR (500 MHz, CDCl3) δ 5.87 (d, J=8.5 Hz, 1H, carbamate-NH), 4.67 (br d, J=4 Hz, 1H, Boc-NH—CH), 3.79 (br s, 2H, CH—CH2), 3.68-3.62 (m, 9H, morpholine CH2's & OH), 1.44 (s, 9H, t-butyl-CH3); 13C NMR (125 MHz, CDCl3) δ 169.7, 155.7, 80.2, 66.8, 66.7, 64.0, 51.4, 46.3, 42.6, 28.4.

Workup

  1. customThe reaction flask was flushed with N2 (g)
  2. additioncharged with 10% Pd/C (290 mg)
  3. customThe flask was equipped with 2H2 (g) balloons
  4. stirringto stir for 10 h
  5. filtrationThe solution was filtered through a pad of celite
  6. washwashing with additional MeOH (200 mL)
  7. concentrationThe solution was concentrated on a rotary evaporator
  8. customdried under vacuum
  9. customto give 1.2 g of crude material
  10. customThe residue was purified by flash column chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-bd56f238bcc1457685e8d0cbd860c311
Source dataset
uspto-grants-2010_11
Patent number
US07829304B2

Reaction notes

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