p-Toluenesulfonic acid → HCID 86653082, compound

HRID 1254316Notes

Reaction equation

C(OC([NH:8][C@H:9]([CH2:12][N:13]([CH3:23])[C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[CH2:10][OH:11])=O)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC.C(O)C>[NH2:8][C@@H:9]([CH2:10][OH:11])[CH2:12][N:13]([CH3:23])[C:14](=[O:15])[O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 62.5 °C

Procedure

To a solution of (2R)-2-(t-butoxycarbonylamino)-3-(N-methyl-N-(2-(trimethylsilyl)-ethoxycarbonyl)amino)propan-1-ol (0.55 g, 1.58 mmol) in ether (5 mL) was added a solution of p-toluenesulfonic acid (0.31 g, 1.60 mmol) in ethanol (2 mL). Transfer of the p-toluenesulfonic acid was completed with the aid of ether (1 mL). The solution was placed on a rotary evaporator and the ether removed under vacuum at rt. Then, with continuing evacuation, the bath temperature was raised to 60-65° C. for 30 min, during which gas evolution was evident. The solid residue was dissolved in 1 N aq NaOH solution (5 mL) and extracted with CH2Cl2 (4×5 mL). The combined organic layers were washed with brine and dried over Na2SO4. Solvent was removed in vacuo to give (2-(trimethylsilyl)ethyl) (R)-2-amino-3-hydroxypropyl-methylcarbamate (0.35 g, 90%) as a free amine, which was without purification. MS m/z 249 (M+H+).

Workup

customThe solution was placed on a rotary evaporator
customthe ether removed under vacuum at rt
dissolutionThe solid residue was dissolved in 1 N aq NaOH solution (5 mL)
extractionextracted with CH2Cl2 (4×5 mL)
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
customSolvent was removed in vacuo

Sources & evidence

ORD record: ord-04e6fc55e76f4177bde7439f89223bbc
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455521B2

Reaction notes

Loading…