N-(tert-butoxycarbonylamino)-phenylalanine → (3R,4S)-3-amino-1-(2-amino-3-phenylpropyl)-4-(3-boronopropyl)pyrrolidine-3-carboxylic acid

HRID 61406Notes

Reaction equation

HRID 61406 reaction equation
Cl.Cl.Cl.[NH2:4][C@:5]1([C:26]([OH:28])=[O:27])[C@@H:9]([CH2:10][CH2:11][CH2:12][B:13]([OH:15])[OH:14])[CH2:8][N:7]([CH2:16][CH:17]([NH2:25])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6]1.C(OC(NN[C@H](C(O)=O)CC1C=CC=CC=1)=O)(C)(C)C>O>[NH2:4][C@:5]1([C:26]([OH:28])=[O:27])[C@@H:9]([CH2:10][CH2:11][CH2:12][B:13]([OH:15])[OH:14])[CH2:8][N:7]([CH2:16][CH:17]([NH2:25])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 67512669N-(tert-butoxycarbonylamino)-phenylalanineHCID 67513125HCID 67513125, compound

Product 1

HCID 57331634(3R,4S)-3-amino-1-(2-amino-3-phenylpropyl)-4-(3-boronopropyl)pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(3R,4S)-3-Amino-1-(2-amino-3-phenylpropyl)-4-[3-(dihydroxyboryl)propyl]pyrrolidine-3-carboxylic acid trihydrochloride (mixture of two diastereomers; each a racemate) is prepared in a manner analogous to that set forth in Example 54, Steps 1-3 except commercial N-(tert-butoxycarbonylamino)-phenylalanine is used in place of tert-butyl 7-chloro-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate. 1H NMR (0.1M DCl in D2O, 400 MHz) δ 7.30 (m, 5 H), 4.41 (s, 2 H), 4.00 (m, 3 H), 3.85 (m, 2 H), 3.75 (m, 1 H), 3.41 (m, 2 H), 2.86 (m, 1H), 2.69 (m, 1 H), 1.60 (m, 1 H), 1.27 (m, 3 H), 0.67 (m, 2 H). ESI+MS found for C17H28BN3O4 m/z 332.2 (M−18+H), 314.2 (M−36 (2 H2O)+H); ESI−MS m/z 330.2 (M−18 (H2O)−H).

Sources & evidence

ORD record
ord-8ed43fc639384d0ba97d0ab626d97afa
Source dataset
uspto-grants-2016_09
Patent number
US09440995B2

Reaction notes

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