D(-)-Leucinol → 5-((2S)-2-({(2S)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-{[(1R)-1-(hydroxymethyl)-3-methylbutyl]amino}-3-oxopropyl)-2-(carboxymethoxy)benzoic Acid

HRID 2188430Notes

Reaction equation

HRID 2188430 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]([OH:16])=O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:41][C@@H:42]([CH2:47][OH:48])[CH2:43][CH:44]([CH3:46])[CH3:45]>>[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:41][C@@H:42]([CH2:47][OH:48])[CH2:43][CH:44]([CH3:46])[CH3:45])=[O:16])[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])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 2724002D(-)-LeucinolHCID 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 571576615-((2S)-2-({(2S)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-{[(1R)-1-(hydroxymethyl)-3-methylbutyl]amino}-3-oxopropyl)-2-(carboxymethoxy)benzoic Acid

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 and D-leucinol (37 uL) according to Method A to give the title compound (51 mg). 1H-NMR (400 MHz, CD3OD) d 7.79 (s, 1H), 7.44 (d, J=8.1 Hz, 1H), 7.29-7.18 (m, 5H), 7.04 (d, J=8.5 Hz, 1H), 4.80 (s, 2H), 4.55 (t, J=7.0 Hz, 1H), 4.25 (dd, J=4.8 Hz, J=9.5 Hz, 1H), 3.86 (m, 1H), 2.75 (dd, J=9.5 Hz, J=13.5 Hz, 1H), 1.35 (s, 9H), 0.82 (m, 6H); IR (KBr) 3312, 2958, 1639 cm−1; HRMS m/z 629.2926 (calc. of monoisotopic mass for C32H43N3O10 gives 629.2948).

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-e073b2817a0743b58d43cc582f8187ea
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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