Acetic Acid → HCID 10831118, compound

HRID 1531697Notes

Reaction equation

[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH:10]=[C:11]2[N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[CH2:3]1.O.NN.C(O)(=O)C>CCO>[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of Compound 6 (200 mg, 0.590 mmol), hydrazine hydrate (0.57 ml, 1.77 mmol), and acetic acid (0.35 ml) in EtOH (20 ml) was heated at 80° C. while a stream of air was passed through the solution for 6 h. The reaction mixture was concentrated to about 10 ml and after cooling, it was diluted with EtOAc (30 ml) followed by washing with saturated aqueous NaHCO3 (10 ml×2), and brine (10 ml×2), dried (Na2SO4) and concentrated to give a crude product (190 mg). This was purified by FCC (silica gel, CH2Cl2/EtOH, (30:1)) to give the Compound 8 (150 mg, 10-74.6%), mp 246-248° C. 1H NMR (300 MHz, CDCl3): δ 0.56 (3H, s, 18-Me), 1.01 (3H, s, 19-Me), 3.53 (1H, m, 3α-H), 4.19 (1H, t, J 9.6 Hz, 17a-H), 5.37 (1H, d, J=5.2 Hz, 6-H), 7.93 (1H, s, 3′-H) and 8.10 (1H, s, 5′-H). Analysis calculated for C21H31ON3: C, 73.85; H, 9.16; N, 12.31. Found: C, 73.75; H, 9.40; N, 12.28.

Workup

concentrationThe reaction mixture was concentrated to about 10 ml
temperatureafter cooling
additionit was diluted with EtOAc (30 ml)
washby washing with saturated aqueous NaHCO3 (10 ml×2), and brine (10 ml×2)
dry with materialdried (Na2SO4)
concentrationconcentrated
customto give a crude product (190 mg)
customThis was purified by FCC (silica gel, CH2Cl2/EtOH, (30:1))

Sources & evidence

ORD record: ord-31938cbb37d44b67955a6f431c61c2ba
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200965B1

Reaction notes

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