Dipentylamine → HCID 18476901, compound

HRID 2188450Notes

Reaction equation

HRID 2188450 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].[CH2:41]([NH:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:42][CH2:43][CH2:44][CH3:45]>>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:10]([NH:12][CH:13]([C:14]([N:46]([CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[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 16316DipentylamineHCID 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 18476901HCID 18476901, compoundYield 53.1%

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 (100 mg, 0.18 mmol) and dipentylamine (46 mg, 0.29 mmol) according to Method C with HPLC purification to give the title compound (64 mg). 1H-NMR (400 MHz, CD3OD) δ 0.90 (m, 6H) 1.14-1.53 (m, 21H) 2.65-2.82 (m, 1H) 2.86-3.38 (m, 7H) 4.30 (m, 1H) 4.80 (d, 2H) 4.94 (m, 1H) 7.02 (m, 1H) 7.21 (m, 5H) 7.35-7.35 (dd, 1H) 7.76 (dd, 1H); HRMS m/z 669.3634 (calc. of monoisotopic mass for C36H51N3O9 gives 669.3625); mp 87-90° C.

Workup

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

Sources & evidence

ORD record
ord-2725e42fb58b40778a07bdea51c123ea
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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