Trifluoroacetic acid → HCID 59997296, compound

HRID 1815581Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([N:13]([O:41][CH:42]([CH2:45][CH3:46])[CH2:43][CH3:44])[CH2:14][C@@H:15]([OH:40])[C@@H:16]([NH:32]C(=O)OC(C)(C)C)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:20][CH:19]=3)(=[O:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[NH2:32][C@@H:16]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:23]=1)[C@H:15]([OH:40])[CH2:14][N:13]([O:41][CH:42]([CH2:43][CH3:44])[CH2:45][CH3:46])[S:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)(=[O:11])=[O:12]

Participants

Conditions

Temperature: 5 °C

Procedure

To an ice cold solution of tert-Butyl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(1-ethylpropoxy)amino]-1-[4-(benzyloxy)benzyl]-2-hydroxypropylcarbamate (1.5 g, 2.3 mmol) in dichloromethane (15 mL) was added trifluoroacetic acid (10 mL). After stirring at 5° C. for 3 h, the reaction was concentrated in vacuo, taken up in ethyl acetate (80 mL), washed with saturated sodium bicarbonate (2×50 mL), dried (magnesium sulfate) and concentrated in vacuo to afford the title compound (1.27 g, quant.) as an off-white foam. 1H NMR (DMSO-d6): δ 0.77 (6H, dt), 1.07-1.72 (4H, m), 1.82 (2H, br), 2.28 (1H, t), 2.58-3.05 (4H, m), 3.43-3.53 (1H, m), 3.95-4.03 (1H, m), 4.86 (1H, br s), 5.01 (2H, s), 6.16 (2H, s), 6,86 (2H, d), 7.03 (2H, d), 7.12-7.40 (8H, m);

Workup

concentrationthe reaction was concentrated in vacuo
washwashed with saturated sodium bicarbonate (2×50 mL)
dry with materialdried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7f531667fb754a0ea2c781eeeb4a64c5
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878728B1

Reaction notes

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