(S)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-[(tert-butoxy)carbonyl]propanoic acid

Base Information

Chemical Name:(S)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-[(tert-butoxy)carbonyl]propanoic acid
CAS No.:637337-67-8
Molecular Formula:C₁₇H₂₃NO₆
Molecular Weight:337.373
Hs Code.:

Synonyms:(S)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-[(tert-butoxy)carbonyl]propanoic acid

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Chemical Property of (S)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-[(tert-butoxy)carbonyl]propanoic acid

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Technology Process of (S)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-[(tert-butoxy)carbonyl]propanoic acid

There total 9 articles about (S)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-[(tert-butoxy)carbonyl]propanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

: 637337-18-9
tert-butyl (S)-3-({[(benzyloxy)carbonyl]amino}methyl)-4-[(R)-4-(1-methylethyl)-2-oxo-5,5-diphenyloxazolidin-3-yl]-4-oxobutanoate

: 637337-67-8
(S)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-[(tert-butoxy)carbonyl]propanoic acid

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 2h;
DOI:10.1002/hlca.200490142

Reference yield:

: 865704-46-7
tert-butyl 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoate

: 637337-67-8
(S)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-[(tert-butoxy)carbonyl]propanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaI; NaHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 60 percent / tetrahydrofuran / 4 h / -95 - -75 °C

2.1: 100 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760 Torr

3.1: Et₃N / tetrahydrofuran / 0.5 h / -15 - 20 °C

4.1: aq. NaN₃ / tetrahydrofuran / 1 h / 0 °C

5.1: toluene / Heating

6.1: 0.82 g / toluene / Heating

7.1: 94 percent / H₂O₂; aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

With lithium hydroxide; sodium azide; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; toluene; 5.1: Curtius rearrangement;
DOI:10.1055/s-2005-865362

Reference yield:

: 865704-48-9
1-benzyl 5-tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}pentanedioate

: 637337-67-8
(S)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-[(tert-butoxy)carbonyl]propanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760 Torr

2: Et₃N / tetrahydrofuran / 0.5 h / -15 - 20 °C

3: aq. NaN₃ / tetrahydrofuran / 1 h / 0 °C

4: toluene / Heating

5: 0.82 g / toluene / Heating

6: 94 percent / H₂O₂; aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

With lithium hydroxide; sodium azide; hydrogen; dihydrogen peroxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; toluene; 4: Curtius rearrangement;
DOI:10.1055/s-2005-865362