2-Amino-1-(3-phenoxyphenyl)ethan-1-ol → 5-((2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-{[2-hydroxy-2-(3-phenoxyphenyl)ethyl]amino}-3-oxopropyl)-2-(carboxymethoxy)benzoic Acid

HRID 2188453Notes

Reaction equation

HRID 2188453 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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:30]([O:32]C)=[O:31])[CH:19]=1)[C:14](O)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:41][CH2:42][CH:43]([C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([O:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:46]=1)[OH:44]>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:10]([NH:12][C@H:13]([C:14]([NH:41][CH2:42][CH:43]([OH:44])[C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([O:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:46]=1)=[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:30]([OH:32])=[O:31])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 156336112-Amino-1-(3-phenoxyphenyl)ethan-1-olHCID 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 570718465-((2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-{[2-hydroxy-2-(3-phenoxyphenyl)ethyl]amino}-3-oxopropyl)-2-(carboxymethoxy)benzoic AcidYield 21.1%

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 (96 mg, 0.16 mmol) and 2-amino-1-(3-phenoxyphenyl)-1-ethanol (45 mg, 0.20 mmol) according to Method C with HPLC purification to give the title compound (25 mg) as a diasteromeric mixture. 1H-NMR (400 MHz, CD3OD) d 7.59 (d, J=1.7 Hz, 1H), 6.87 (dd, J=1.2 Hz, J=8.3 Hz, 1H), 4.66 (m, 3H), 4.55 (t, J=7.0 Hz, 1H), 4.23 (m, 1H), 3.02 (m, 2H), 3.52 (m, 1H), 2.90 (m, 1H), 2.69 (m, 1H), 1.34 (s, 9H); HRMS m/z 741.2925 (calc. of monoisotopic mass for C40H43N3O11 gives 741.2898).

Workup

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

Sources & evidence

ORD record
ord-25928ebe23cc4cfbb366e75ee9ee44ef
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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