Water → 3-((Tert-butoxycarbonyl)amino)propyl methanesulfonate

HRID 713680Notes

Reaction equation

HRID 713680 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][OH:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].O>ClCCl>[CH3:20][S:21]([O:12][CH2:11][CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 114141093-((Tert-butoxycarbonyl)amino)propyl methanesulfonateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(Boc-amino)-propanol (10 g, 57.5 mmol) in dichloromethane (100 mL) was added triethylamine (11.6 g, 115 mmol) at 0° C., then methanesulfonyl chloride (7.9 g, 69 mmol) was dropwise added. The resulting mixture was stirred for 1 hour at 0° C., poured into water, and then extracted with dichloromethane for 3 times (100 mL for each time). The organic phases were combined, dried and concentrated to afford the product 3-(tert-butyloxycarbonylamino)propyl methanesulfonate (13.1 g, yield: 94%). The characterization of the resulting product was as follows: 1HNMR (400 MHz, CDCl3): δ=4.76 (s, 1H), 4.26 (t, J=6.4 Hz, 2H), 3.22-3.24 (m, 2H), 3.00 (s, 3H), 1.89-1.92 (m, 2H), 1.41 (s, 9H).

Workup

  1. extractionextracted with dichloromethane for 3 times (100 mL for each time)
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ec67da500ced40778047a65ae31f5524
Source dataset
uspto-grants-2015_11
Patent number
US09186318B2

Reaction notes

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