Di-tert-butyl dicarbonate → HCID 54112853, compound

HRID 1647857Notes

Reaction equation

HRID 1647857 reaction equation
C(OC(OC(C)(C)C)=O)([O:3][C:4](C)(C)[CH3:5])=O.Cl.[OH:17][C@H:18]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:19][NH:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([OH:33])=[O:32])=[CH:26][CH:25]=1>C(O)(C)(C)C.[OH-].[Na+]>[C:4]([O:17][C@H:18]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:19][NH:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([OH:33])=[O:32])=[CH:26][CH:25]=1)(=[O:3])[CH3:5]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 158793ZD 2079

Product 1

HCID 54112853HCID 54112853, compoundYield 639.9%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

Di-t-butyl dicarbonate (1.25 g) in t-butanol (15 ml) was added to a stirred solution of (R)-4-[2-(2-hydroxy-2-phenylethylamino)ethoxy]phenylacetic acid hydrochloride (2.0 g) in 1N aqueous sodium hydroxide (30 ml). The reaction mixture was stirred for 90 minutes at 20° C. The solvent was removed under reduced pressure. Water (20 ml) was added to the residue and the solution was acidified with 2N aqueous citric acid. The product was extracted into 5% methanol in dichloromethane (5×20 ml). The extracts were dried and the solvent removed under reduced pressure to yield N-t-butoxycarbonyl-(R)-[4-[2-(2-hydroxy-2-phenylethylamino)ethoxy]phenylacetic acid as a glass (13 g); [α]25D =-6.2° (c=1.0 in methanol).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionWater (20 ml) was added to the residue
  3. extractionThe product was extracted into 5% methanol in dichloromethane (5×20 ml)
  4. customThe extracts were dried
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b1be821d3db141ad80ab1f6b4ee8d3ed
Source dataset
uspto-grants-1995_07
Patent number
US05434184

Reaction notes

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