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Water → tert-butyl N-{2-[2-(methanesulfonyloxy)ethoxy]ethyl}carbamate

HRID 536266
Notes
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Reaction equation

HRID 536266 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>ClCCl>[CH3:22][S:23]([O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:14])(=[O:25])=[O:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 52204702-(2-Boc-aminoethoxy)ethanol

Product 1

HCID 12106196tert-butyl N-{2-[2-(methanesulfonyloxy)ethoxy]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl[2-(2-hydroxyethoxy)ethyl]carbamate (Step 1, 3.73 g, 18 mmol) was diluted in dichloromethane (75 mL) and cooled to 0° C. Triethylamine (3.0 mL, 22 mmol) was added, followed by methanesulfonyl chloride (1.7 mL, 22 mmol). After stirring at rt for 1 h, water was added. The aqueous layer was separated and extracted with dichloromethane. The combined organics were dried and concentrated in vacuo to afford the title compound as an oil. 1H NMR (CDCl3) δ: 1.44 (9H, s), 3.06 (3H, s), 3.32 (2H, m), 3.56 (2H, t), 3.72 (2H, m), 4.36 (2H, m).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with dichloromethane
  3. customThe combined organics were dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a380f3b5c43e4ad0bbc6b5a8601639da
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859572B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes