Cyclopropylamine → (2S)-1-[(3R)-3-amino-4-phenylbutanoyl]-N-({5-chloro-2-[(cyclopropylcarbamoyl)methoxy]phenyl}methyl)pyrrolidine-2-carboxamide

HRID 11419Notes

Reaction equation

HRID 11419 reaction equation
C(=O)(OC(C)(C)C)N.[NH2:9][C@H:10]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:11][C:12]([N:14]1[CH2:34][CH2:33][CH2:32][C@H:15]1[C:16]([NH:18][CH2:19][C:20]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:21]=1[O:22][CH2:23][C:24]([OH:26])=O)=[O:17])=[O:13].[CH:42]1([NH2:45])[CH2:44][CH2:43]1>CN(C=O)C>[NH2:9][C@H:10]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:11][C:12]([N:14]1[CH2:34][CH2:33][CH2:32][C@H:15]1[C:16]([NH:18][CH2:19][C:20]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:21]=1[O:22][CH2:23][C:24]([NH:45][CH:42]1[CH2:44][CH2:43]1)=[O:26])=[O:17])=[O:13]

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 77922tert-Butyl carbamateHCID 58682734HCID 58682734, compound

Product 1

HCID 10164624(2S)-1-[(3R)-3-amino-4-phenylbutanoyl]-N-({5-chloro-2-[(cyclopropylcarbamoyl)methoxy]phenyl}methyl)pyrrolidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 46 mg (0.08 mmol) of the tert butyl carbamate of {2-[({1-[(3R)-3-amino-4-phenylbutanoyl]-L-prolyl}amino)methyl]-4-chlorophenoxyacetic acid and 0.0055 mL (0.096 mmol) of cyclopropylamine in DMF were coupled and deprotected as described for Example 1, Step C and D to give 25 mg of the title compound. 1H NMR (400 MHz, CD3OD) δ 7.32–7.10 (m, 7H), 6.95 (d, 0.2H, J=8 Hz), 6.85 (d, 0.8H, J=8 Hz), 4.55–4.22 (m, 5H), 3.61–3.35 (m, 3H), 2.82–2.50 (m, 4H), 2.38–2.10 (m, 2H), 2.07–1.80 (m, 3H), 0.75–0.58 (m, 4H).

Sources & evidence

ORD record
ord-ad431575cf5e4313ab0e837e19d4f850
Source dataset
uspto-grants-2006_08
Patent number
US07098239B2

Reaction notes

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