Ammonium formate → HCID 131733854, compound

HRID 708547Notes

Reaction equation

C([NH:8][CH2:9][CH2:10][C@H:11]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:12][O:13][Si:14]([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[NH2:8][CH2:9][CH2:10][C@H:11]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:12][O:13][Si:14]([C:27]([CH3:30])([CH3:28])[CH3:29])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To (S)-tert-butyl (4-(benzylamino)-1-((tert-butyldiphenylsilyl)oxy)butan-2-yl)carbamate (8.0 g, 15.0 mmol) in MeOH (100 mL) was added ammonium formate (9.47 g, 150 mmol) and Pd(OH)2 (1.054 g, 1.502 mmol). The reaction mixture was stirred at 70° C. for 1.5 h then cooled to rt and filtered through a celite, eluting with MeOH/EtOAc (1:2, ˜800 mL). The filtrate was concentrated in vacuo to afford the title compound (7 g) of a light brown residue which was used as such without further purification. LCMS: Rt=0.95 min, m/z=443.2 (M+1) Method 2m_acidic.

Workup

temperaturethen cooled to rt
filtrationfiltered through a celite
washeluting with MeOH/EtOAc (1:2, ˜800 mL)
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-30adb1146abf49339753b5a596280222
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174978B2

Reaction notes

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