Hydrochloric Acid → Methyl 4-[2(S)-amino-1-propoxy]phenylacetate

HRID 1901210Notes

Reaction equation

HRID 1901210 reaction equation
C(OC([NH:8][C@@H:9]([CH3:12])[CH2:10][OH:11])=O)(C)(C)C.O[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.Cl>O1CCOCC1.CO.C1C=CC=CC=1>[NH2:8][C@@H:9]([CH3:12])[CH2:10][O:11][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 22867084Methyl 4-[2(S)-amino-1-propoxy]phenylacetate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Following a procedure similar to that described in Preparation 27, but using 15.8 g of (S)-2-t-butoxycarbonylamino-1-propanol, 10.0 g of methyl 4-hydroxyphenylacetate, 24 g of triphenylphosphine, 70 ml of dry benzene, 15.7 g of diethyl azodicarboxylate, 50 ml of methanol and 70 ml of a 4N solution of hydrogen chloride in dioxane, the title compound was obtained.

Workup

  1. customthat described in Preparation 27

Sources & evidence

ORD record
ord-d34539dc5c484f589f5e8d14243b77fa
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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