1-Naphthaldehyde → (S)-3-(4-Bromo-phenyl)-2-{2-chloro-5-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl ester

HRID 1784241Notes

Reaction equation

HRID 1784241 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([NH:13][C:14](=[O:23])[C:15]1[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:16]=1[Cl:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1.[C:25]1([CH:35]=O)[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(Cl)Cl>ClCCCl.C1COCC1>[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([NH:13][C:14](=[O:23])[C:15]1[CH:20]=[C:19]([NH:21][CH2:35][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=[CH:27][CH:26]=2)[CH:18]=[CH:17][C:16]=1[Cl:22])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([Br:12])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 61951-NaphthaldehydeHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 68861548(S)-2-(5-Amino-2-chloro-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester

Product 1

HCID 68862805(S)-3-(4-Bromo-phenyl)-2-{2-chloro-5-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl esterYield 62.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-3-(4-Bromo-phenyl)-2-{2-chloro-5-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl ester (264 mg) was prepared from (S)-2-(5-amino-2-chloro-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester (316 mg, 0.77 mmol) and 1-naphthaldehyde (0.231 mL, 1.7 mmol) according to Procedure G, except for the following: the reaction was done in 15 mL DCE and 2 mL THF, two additional equiv. NaBH(OAc)3 were added after 2 h and an adapted work-up. After reaction completion, 100 mL of DCM was added and the organic washed with saturated sodium bicarbonate, dried over sodium sulfate, and evaporated. The crude material was purified over silica gel (8:2, DCM-hexanes).

Workup

  1. additionwas added
  2. washthe organic washed with saturated sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude material was purified over silica gel (8:2, DCM-hexanes)

Sources & evidence

ORD record
ord-86e11b55b99c44259c73f074def85c89
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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