2-[3-(tert-butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoic acid benzhydryl ester

Base Information

• Chemical Name: 2-[3-(tert-butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoic acid benzhydryl ester
• CAS No.: 223270-77-7
• Molecular Formula: C₂₈H₃₇NO₆
• Molecular Weight: 483.605

Synonyms:2-[3-(tert-butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoic acid benzhydryl ester

Chemical Property of 2-[3-(tert-butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoic acid benzhydryl ester

Chemical Property:

Purity/Quality:

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Technology Process of 2-[3-(tert-butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoic acid benzhydryl ester

There total 3 articles about 2-[3-(tert-butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoic acid benzhydryl 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:

(R)-2-hydroxy-4-methylpentanoic acid (20312-37-2,498-36-2) → 2-[3-(tert-butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoic acid benzhydryl ester (223270-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / PhI(OAc)2, I₂ / -10 °C

2: EDCI, DMAP, TEA

With dmap; [bis(acetoxy)iodo]benzene; TEA; iodine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;

DOI:10.1016/S0960-894X(99)00038-4

Reference yield:

(R)-leucine (328-38-1,21675-61-6,25248-98-0,70-45-1) → 2-[3-(tert-butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoic acid benzhydryl ester (223270-77-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent / NaNO₂, H₂SO₄ / H₂O

2: 70 percent / PhI(OAc)2, I₂ / -10 °C

3: EDCI, DMAP, TEA

With dmap; [bis(acetoxy)iodo]benzene; TEA; sulfuric acid; iodine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium nitrite; In water;

DOI:10.1016/S0960-894X(99)00038-4

Reference yield:

N-t-butoxycarbonyl-N-methyl-β-alanine (124072-61-3) + Diphenylmethyl (2R)-2-hydroxy-4-methylpentanoate (168069-99-6) → 2-[3-(tert-butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoic acid benzhydryl ester (223270-77-7)

Guidance literature:

With dmap; TEA; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; Yield given;

DOI:10.1016/S0960-894X(99)00038-4

upstream raw materials:

N-t-butoxycarbonyl-N-methyl-β-alanine

Diphenylmethyl (2R)-2-hydroxy-4-methylpentanoate

(R)-leucine

(R)-2-hydroxy-4-methylpentanoic acid

Downstream raw materials:

(S)-2-{(R)-2-[3-(tert-Butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoylamino}-4-methyl-pentanoic acid (S)-1-[((S)-1-benzyloxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester

(S)-4-Methyl-2-[(R)-4-methyl-2-(3-methylamino-propionyloxy)-pentanoylamino]-pentanoic acid (S)-1-[((S)-1-benzyloxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester

(S)-4-Methyl-2-[(R)-4-methyl-2-(3-methylamino-propionyloxy)-pentanoylamino]-pentanoic acid (S)-1-[((S)-1-carboxy-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester

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