(R)-2-(4-Hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl ester → (R)-4-(2-t-Butoxycarbonylaminopropyl)phenoxymethyl-(3-benzyloxypropyl)phosphinic acid, n-butyl ester

HRID 1533Notes

Reaction equation

HRID 1533 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][P:12]([CH2:19][O:20]S(C1C=CC(Cl)=CC=1)(=O)=O)(=[O:18])[O:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C@H:39]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH3:40])=[CH:34][CH:33]=1>>[C:44]([O:43][C:42]([NH:41][CH:39]([CH3:40])[CH2:38][C:35]1[CH:34]=[CH:33][C:32]([O:20][CH2:19][P@:12]([CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:18])[O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:37][CH:36]=1)=[O:48])([CH3:47])([CH3:45])[CH3:46]

Participants

3

Reactant 2

HCID 59909921(R)-2-(4-Hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl esterHCID 867521953-Benzyloxypropyl-(4-chlorobenzenesulfonyloxymethyl)phosphinic acid, n-butyl ester

Product 1

HCID 86752196(R)-4-(2-t-Butoxycarbonylaminopropyl)phenoxymethyl-(3-benzyloxypropyl)phosphinic acid, n-butyl ester

Procedure

The title compound was prepared from 3-benzyloxypropyl-(4-chlorobenzenesulfonyloxymethyl)phosphinic acid, n-butyl ester and (R)-2-(4-hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl ester according to the method described in Procedure 24. The crude product was purified by chromatography, eluting with dichloromethane containing 3% methanol, to give an oil.

Workup

  1. customThe crude product was purified by chromatography
  2. washeluting with dichloromethane containing 3% methanol
  3. customto give an oil

Sources & evidence

ORD record
ord-dc474815e92e4518a4bce138d4d23348
Source dataset
uspto-grants-1998_03
Patent number
US05726165

Reaction notes

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