Triethylamine → HCID 18341276, compound

To a solution of (S)-2-amino-3-phenyl-1-propanol (1.00 g, 6.61 mmol) and triethylamine (1 mL, 7.17 mmol) in THF (70 mL) at −78° C. was added dropwise bromoacetyl bromide (0.60 mL, 6.9 mmol). After 1.25 hours at −78° C., the resultant mixture was partitioned between 1M pH7 phosphate buffer (100 mL) and hexanes (100 mL). The aqueous layer was extracted with EtOAc:hex (2:1, 50 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give 1.59 g (85%) of 2-bromo-N-(1(S)-hydroxymethyl-2-phenylethyl)acetamide as a solid, mp 83-5° C. 1H NMR (DMSO-d6): δ 8.15 (d, 1H, J=8.1 Hz), 7.32-7.11 (m, 5H), 4.82 (t, 1H, J=5.3 Hz), 3.83-3.74 (m, 3H), 2.80 (dd, 1H, J=5.9, 13.6 Hz), 2.59 (dd, 1H, J=8.9, 13.6 Hz). Anal. Calculated for C11H14NO2Br: C, 48.55; H, 5.19; N, 5.15; Br, 29.36. Found: C, 48.69; H, 5.13; N, 5.13; Br, 29.30.

1. customthe resultant mixture was partitioned between 1M pH7 phosphate buffer (100 mL) and hexanes (100 mL)
2. extractionThe aqueous layer was extracted with EtOAc
3. washThe combined organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated

ORD record

ord-8a36d55a9dcf4ee0b6423680e04106d4

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174915B1