Water → HCID 18771212, compound

HRID 479600Notes

Reaction equation

HRID 479600 reaction equation
[C:1]1(=[O:5])[O:4][CH2:3][CH2:2]1.[CH2:6]([C:8]1[C:9]([C:31](=[O:35])[C:32]([NH-:34])=[O:33])=[C:10]2[N:15]([C:16]=1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:14]=[CH:13][C:12]([OH:30])=[CH:11]2)[CH3:7].[CH3:36][C:37](C)([O-])C.[K+].O>O1CCCC1>[C:1]([CH2:36][CH2:37][O:30][C:12]1[CH:13]=[CH:14][N:15]2[C:10]([CH:11]=1)=[C:9]([C:31](=[O:35])[C:32]([NH2:34])=[O:33])[C:8]([CH2:6][CH3:7])=[C:16]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([O:4][CH2:3][CH3:2])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 2365Beta-PropiolactoneHCID 23665647Potassium tert-butoxideHCID 178436942HCID 178436942, compound

Product 1

HCID 18771212HCID 18771212, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Propiolactone (25 mg, 0.336 m mol) was added dropwise to a solution of 65c (133.7 mg, 0.336 m mol) and potassium t-butoxide (37.6 mg, 0.336 m mol) in tetrahydrofuran (4 ml) under nitrogen. The mixture was stirred for 21 hr. Water was added. The mixture was washed with ethyl acetate. The aqueous phase was acidified with hydrochloric acid. The precipitate was collected with filtration to give 70b, 96.2 mg (60.9%). Mp, 99-108° C. (dec.). IR nmax (KBr) 3700-2400, 3182, 2968, 2931, 1719, 1677, 1644 cm−1. 1H NMR (CDCl3) δ 1.19 (3H, t, J=7.5 Hz), 2.80 (2H, t, J=6.3 Hz), 2.92 (2H, q, J=7.5 Hz), 4.08 (2H, s), 4.30 (2H, t, J=6.3 Hz), 6.35 (1H, dd, J=2.7, 7.8 Hz), 6.84 (1H, d, J=7.8 Hz), 7.12-7.53 (9H, m), 7.72 (1H, d, J=2.7 Hz). Analyses: Calc'd for C28H26N2O5.1.2H2O: C, 68.34; H, 5.82; N, 5.69. Found: C, 68.40; H, 5.76; N, 5.43.

Workup

  1. washThe mixture was washed with ethyl acetate
  2. filtrationThe precipitate was collected with filtration

Sources & evidence

ORD record
ord-8cc9b168ddf6413081780c5ee671f321
Source dataset
uspto-grants-2003_11
Patent number
US06645976B1

Reaction notes

Loading…