Dimethyl Sulfoxide → HCID 57451421, compound

HRID 1444576Notes

Reaction equation

C(Cl)(=O)C(Cl)=[O:3].CS(C)=O.[C:11]([C:18]([CH3:23])([CH3:22])[CH:19]([NH2:21])O)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N(CC)CC)C.P([O-])(O)(O)=O.[Na+]>C(Cl)Cl>[C:11]([C:18]([CH3:23])([CH2:19][NH2:21])[CH:22]=[O:3])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

Conditions

Temperature: -60 °C

Procedure

A solution of oxalyl chloride (15.24 g, 120 mmol) in 200 mL of MeCl2 was stirred and cooled to −60° C. followed by the drop wise addition of dimethylsulfoxide (19.7 g, 252 mmol) in 60 ml of MeCl2. After 10 min, a solution of 2-Boc-amino-2-methyl-1-propanol (18.9 g, 100 mmol) in MeCl2 (60 ml) was added drop wise at −70° C. The reaction mixture was allowed to warm to −40° C. for 10 min followed by cooling to −70° C. before the addition of a solution of triethylamine (28.28 g, 280 mmol) in MeCl2 (60 mL). The reaction mixture was allowed to warm to room temperature over a two-hour period and 40 mL of saturated sodium dihydrogen phosphate was added. The organic layer was washed with brine and dried over MgSO4. The solvent was removed to yield 17.3 g of 2-Boc-amino-2-methylpropionaldehyde.

Workup

temperatureto warm to −40° C. for 10 min
temperatureto warm to room temperature over a two-hour period
washThe organic layer was washed with brine
dry with materialdried over MgSO4
customThe solvent was removed

Sources & evidence

ORD record: ord-864dd8b628974b97b7f4a2850c11bc40
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662849B2

Reaction notes

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