N-Methylpentylamine → HCID 18476987, compound

HRID 2188457Notes

Reaction equation

HRID 2188457 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:34]C1C=CC=CC=1)[C:10]([NH:12][C@@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([O:28]C)=[O:27])=[C:20](C(OC)=O)[CH:19]=1)[C:14](O)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:41][NH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]>>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:34][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10]([NH:12][CH:13]([C:14]([N:42]([CH3:41])[CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[O:15])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([OH:28])=[O:27])=[C:20]([CH:19]=1)[C:6]([OH:7])=[O:5])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 117479N-MethylpentylamineHCID 57019224(2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[3-(methoxycarbonyl)-4-(2-methoxy-2-oxoethoxy)phenyl]propanoic acid

Product 1

HCID 18476987HCID 18476987, compoundYield 59.7%

Procedure

Synthesis was performed from (2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[3-(methoxycarbonyl)-4-(2-methoxy-2-oxoethoxy)phenyl]propanoic acid (100 mg, 0.18 mmol) and N-methylamylamine (29 mg, 0.29 mmol) according to Method C with HPLC purification to give the title compound (33 mg). 1H-NMR (400 MHz, CD3OD) d 7.76 (s, 1H), 7.5-7.15 (m, 6H), 7.04 (d, 1H), 5.02 (m, 1H), 4.81 (s, 2H), 4.28 (m, 1H), 3.25-2.7 (m, 9H), 1.10-1.5 (m, 15H), 0.89 (t, 3H); HRMS m/z 613.2982 (calc. of monoisotopic mass for C32H43N3O9 gives 613.2999).

Workup

  1. customSynthesis
  2. customaccording to Method C with HPLC purification

Sources & evidence

ORD record
ord-2f4914b3ff5e46498c49265e03d6be02
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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