Hydrochloric Acid → N-(tert-Butoxy(hydroxy)methylidene)-O-ethylserine

HRID 1504821Notes

Reaction equation

HRID 1504821 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:18][CH3:19].Cl>CS(C)=O.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][O:11][CH2:18][CH3:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 24758Sodium hydride2×HCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 15058451N-(tert-Butoxy(hydroxy)methylidene)-O-ethylserine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)serine (10.26 g, 50.00 mmol) in DMSO (500 mL) was added sodium hydride (2.0 g, 50 mmol) at room temperature. After 1 hour, bromoethane (5.45 g, 50.0 mmol) was added and then additional sodium hydride (2.0 g, 50 mmol) was added immediately. After 16 hours, hydrochloric acid (1.0 M in water, 50 mL, 50 mmol) and water (2 L) were added. The mixture was extracted with ethyl acetate, and the organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford N-(tert-butoxycarbonyl)-O-ethylserine which was used without further purification. MS ESI calc'd. for C10H20NO5 [M+H]+ 234. found 234.

Workup

  1. waitAfter 16 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-83a667d94ec24808b0b9401d6e408b40
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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