Sodium Bicarbonate → HCID 66959084, compound

HRID 403087Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:17][CH:18]([O:35]C(=O)CCl)[C:19](=[O:34])[NH:20][CH2:21][C:22]1[C:27]([O:28][CH3:29])=[CH:26][C:25]([O:30][CH3:31])=[CH:24][C:23]=1[O:32][CH3:33])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].NC(N)=S.C([O-])(O)=O.[Na+]>CCO.C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:17][CH:18]([OH:35])[C:19](=[O:34])[NH:20][CH2:21][C:22]1[C:27]([O:28][CH3:29])=[CH:26][C:25]([O:30][CH3:31])=[CH:24][C:23]=1[O:32][CH3:33])[C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 9 (0.678 g, 1.18 mmol) in EtOH/THF (5/5 mL) was added thiourea (0.269 g, 3.54 mmol) and NaHCO3 (0.297 g, 3.54 mmol). The reaction mixture was stirred and heated to 50° C. for 1.5 h. The solvent was then removed under the reduced pressure and the residue was submitted to FC on silica gel (EtOAc/Hexanes, 45/55 to 60/40, V/V) to give 10 as a mixture of C(4) diastereomers as a waxy white solid (0.543 g, 91%): 1H NMR (200 MHz, CDCl3) δ 7.26 (br s, 1H), 6.13 (s, 1H), 6.12 (s, 1H), 5.45 (d, 1H, J=5.6 Hz), 4.63-4.03 (m, 5H), 3.82, 3.81 (s, s, total 9H), 2.43-1.84 (m, 2H), 1.45 (d, 9H, J=1.2 Hz), 1.43 (s, 9H); 13C NMR (50 MHz, CDCl3) δ 172.6, 172.0, 171.5, 171.3, 161.0, 159.5, 157.3, 156.1, 106.7, 90.8, 82.7, 82.4, 80.8, 80.3, 69.6, 68.5, 55.9, 55.4, 52.0, 51.0, 39.1, 38.5, 32.2, 31.9, 28.3, 28.0; HRMS calcd for C24H39N2O9 (M+H)+: 499.2656. found: 499.2669, 499.2662.

Workup

customThe solvent was then removed under the reduced pressure

Sources & evidence

ORD record: ord-1a189066ca414eb1bfe51d4360563390
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08747809B2

Reaction notes

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