Dichloromethane → HCID 57971685, compound

HRID 2277017Notes

Reaction equation

HRID 2277017 reaction equation
[CH:1]1([O:6][C:7](=[O:31])[C@@H:8]([N:15]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=2)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:32]([O:36][CH:37]([O:39][NH:40][C:41]([C:43]1[S:47][C:46]2[CH:48]=[C:49]([CH:52]=O)[CH:50]=[CH:51][C:45]=2[CH:44]=1)=[O:42])[CH3:38])[CH:33]([CH3:35])[CH3:34].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)Cl>ClCCCl.C(O)(=O)C>[CH:1]1([O:6][C:7](=[O:31])[C@@H:8]([N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][CH2:52][C:49]3[CH:50]=[CH:51][C:45]4[CH:44]=[C:43]([C:41](=[O:42])[NH:40][O:39][CH:37]([O:36][CH2:32][CH:33]([CH3:34])[CH3:35])[CH3:38])[S:47][C:46]=4[CH:48]=3)[CH:25]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 57971656HCID 57971656, compoundHCID 57971713HCID 57971713, compound

Product 1

HCID 57971685HCID 57971685, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To (S)-[(3-Amino-benzyl)-tert-butoxycarbonyl-amino]-phenyl-acetic acid cyclopentyl ester (0.317 g, 0.75 mmol) was added 6-Formyl-benzo[b]thiophene-2-carboxylic acid (1-isobutoxy-ethoxy)-amide (Scheme 7) (0.210 g, 0.65 mmol) in DCE (8 ml). 2 drops of glacial acetic acid were added, and then sodium triacetoxyborohydride (0.170 g, 0.8 mmol). The mixture was stirred for 2 h and then poured into DCM (150 ml). The solution was washed with saturated sodium bicarbonate (50 ml), then dried (MgSO4), concentrated and purified by flash column chromatography to yield the desired product as a pale yellow foam (0.346 g, 73% yield). 1H NMR (300 MHz, CDCl3), δ: 8.35-8.43 (1H, m), 7.56-8.05 (2H, m), 7.01-7.41 (8H, m), 6.90-7.01 (1H, m), 6.42 (1H, dd, J=2.6, 7.9 Hz), 5.25-5.31 (1H, m), 5.12 (1H, q, J=5.2 Hz), 4.40 (1H, d, J 5.4 Hz), 4.00 (1H, dd, J=3.1, 15.8 Hz), 3.60-3.70 (1H, m), 3.35-3.40 (1H, m), 1.33-1.94 (21H, m), 0.98 (3H, d, J=6.6 Hz), 0.97 (3H, d, J=6.6 Hz)

Workup

  1. washThe solution was washed with saturated sodium bicarbonate (50 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-867ecf8209a444ce8bee05fbf4d8d41c
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

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