(3S,4S)-3-(4-benzyloxybenzoylamino)-4-hydroxyazepane-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(3S,4S)-3-(4-benzyloxybenzoylamino)-4-hydroxyazepane-1-carboxylic acid benzyl ester
CAS No.:171230-63-0
Molecular Formula:C₂₈H₃₀N₂O₅
Molecular Weight:474.557
Hs Code.:

Synonyms:(3S,4S)-3-(4-benzyloxybenzoylamino)-4-hydroxyazepane-1-carboxylic acid benzyl ester

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Chemical Property of (3S,4S)-3-(4-benzyloxybenzoylamino)-4-hydroxyazepane-1-carboxylic acid benzyl ester

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Technology Process of (3S,4S)-3-(4-benzyloxybenzoylamino)-4-hydroxyazepane-1-carboxylic acid benzyl ester

There total 12 articles about (3S,4S)-3-(4-benzyloxybenzoylamino)-4-hydroxyazepane-1-carboxylic acid benzyl ester 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:

: 1486-50-6
4-(benzyloxy)benzoic acid chloride

: C₁₄H₂₀N₂O₃

: 171230-63-0
(3S,4S)-3-(4-benzyloxybenzoylamino)-4-hydroxyazepane-1-carboxylic acid benzyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1002/chem.200701991

Reference yield:

: 1486-50-6
4-(benzyloxy)benzoic acid chloride

: trans-3-amino-1-benzyloxycarbonylazepan-4-ol

: 158584-98-6
4-hydroxy-3-[4-(phenylmethoxy)benzoylamino]-1-(phenylmethoxycarbonyl)-hexahydroazepine

: 171230-63-0
(3S,4S)-3-(4-benzyloxybenzoylamino)-4-hydroxyazepane-1-carboxylic acid benzyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 3h;

Reference yield:

: 33439-27-9
N-tosyl-4-piperidone

: 171230-63-0
(3S,4S)-3-(4-benzyloxybenzoylamino)-4-hydroxyazepane-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 98 percent / Br₂ / CH₂Cl₂ / -4 deg C, 90 min; 0 deg C, 30 min; room temperature, 1 h

2: 71 percent / BF₃-Et₂O / CH₂Cl₂ / -5 deg C -> room temperature, 90 min

3: 90 percent / HCl / H₂O; dioxane / 7 h / Heating

4: 73 percent / NaN₃ / acetic acid; dimethylformamide / 19.5 h / Ambient temperature

5: 62 percent / NaBH₄ / ethanol / 0.25 h / 2 - 5 °C

6: 85 percent / PPh₃, diisopropylazodicarboxylate / tetrahydrofuran / 5-10 deg C -> room temperature; room temperature, 17 h

7: 99 percent / NaOH / methanol; H₂O; dioxane / 21 h / Ambient temperature

8: 85 percent / LiAlH₄ / tetrahydrofuran / 0.75 h / 0-2 deg C -> room temperature

9: 68 percent / HBr / H₂O / 1) reflux, 3 h, 2) room temperature, 16 h

10: 88 percent / Et₃N, 18-crown-6 / CH₂Cl₂ / 21 h / Ambient temperature

11: Et₃N / CH₂Cl₂ / 3 h / 0 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; 18-crown-6 ether; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; hydrogen bromide; bromine; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;