(2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[3-(methoxycarbonyl)-4-(2-methoxy-2-oxoethoxy)phenyl]propanoic acid → HCID 70160486, compound

HRID 2188452Notes

Reaction equation

HRID 2188452 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].Cl.[F:42][C:43]1[CH:48]=[C:47]([CH:49]([CH3:52])[CH2:50][NH2:51])[CH:46]=[CH:45][C:44]=1[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:10]([NH:12][C@H:13]([C:14]([NH:51][CH2:50][CH:49]([C:47]1[CH:46]=[CH:45][C:44]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[C:43]([F:42])[CH:48]=1)[CH3:52])=[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])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 57019224(2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[3-(methoxycarbonyl)-4-(2-methoxy-2-oxoethoxy)phenyl]propanoic acidHCID 70160699HCID 70160699, compound

Product 1

HCID 70160486HCID 70160486, compoundYield 42.4%

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 (79 mg, 0.14 mmol) and 2-fluoro-β-methyl-4-biphenylethylamine hydrochloride (45 mg, 0.17 mmol) according to Method C to give the title compound (44 mg). 1H-NMR (400 MHz, CD3OD) d 7.75 (s, 1H), 4.78 (s, 1H), 4.57 (s, 1H), 4.51 (m, 1H), 4.22 (m, 1H), 3.52 (m, 1H), 3.41 (m, 1H), 3.22 (m, 1H), 3.06-2.85 (m, 4H), 2.72 (m, 1H), 1.35 (s, 9H), 1.20 (dd, J=7.0 Hz, J=15.7 Hz, 4H); HRMS m/z 741.3094 (calc. of monoisotopic mass for C41H44FN3O9 gives 741.3062).

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-28632fcd5b9a49958dbbb628e54736b7
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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