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

HRID 1784243Notes

Reaction equation

HRID 1784243 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C@@H:4]([NH:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1.[C:24]1([CH:34]=O)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(Cl)Cl>ClCCCl.C1COCC1>[CH3:1][O:2][C:3](=[O:23])[C@@H:4]([NH:13][C:14](=[O:22])[C:15]1[CH:16]=[CH:17][C:18]([NH:21][CH2:34][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:20]=1)[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 68861436(S)-2-(4-Amino-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester

Product 1

HCID 68860011(S)-3-(4-Bromo-phenyl)-2-{4-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl esterYield 48%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-3-(4-Bromo-phenyl)-2-{4-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl ester (273 mg) was prepared from (S)-2-(4-amino-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester (415 mg, 1.1 mmol) and 1-naphthaldehyde (0.331 mL, 2.4 mmol) according to Procedure G, except for the following: the reaction was done in 15 mL DCE and 5 mL THF, was allowed to stir for 15 min before NaBH(OAc)3was added, was treated with two additional equiv. NaBH(OAc)3 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 triturated with MeOH.

Workup

  1. additionadded
  2. additionwas added
  3. washthe organic washed with saturated sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe crude material was triturated with MeOH

Sources & evidence

ORD record
ord-e2ac4afce6ba4e8f952e9cac82745271
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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